82104-74-3, 1-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
82104-74-3, Example-1 a) Process for the preparation of citalopram (by single Grignard method) : A solution of 4-fluorophenyl magnesium bromide, prepared from 153.33g 4-flour bromobenzene (0.876 moles) and 25.33g magnesium turnings (1.055 moles) and Iodine (0.05g.) in 300mi of dry tetrahydrofuran was added to a suspension of 100g 5- cyanophthalide (0.628 moles) in 900moi dry toluene at-4 to-2¡ãC. After the reaction was completed, the reaction mass was quenched with 100moi 20percent aqueous ammonium chloride solution. Toluene layer was separated and diluted with 100ml of methanol. 12g Sodium borohydride (0. 324moles) was added over a period of one hour at 10-15¡ãC and the same temperature was maintained for additional one hour. The reaction mass was quenched with 200moi ice water and the toluene layer was separated. Toluene layer was washed with water (200ml) and then 10g of paratoluene sulphonic acid was added to toluene layer. The reaction mixture was heated to 80-85¡ãC and the temperature was maintained for additional 3 hours. After the completion of the reaction toluene layer was washed with aq. Sodium hydroxide solution (200ml), water (200moi) and dried over anhydrous sodium sulfate. The toluene solution was then added to a solution of 21grams of sodium hydride dissolved in 400ml of dimethyl sulfoxide and 500 ml toluene under nitrogen atmosphere at 20-25¡ãC. To the resulting solution a solution of 3-N, N,- dimethylaminopropylchloride (53g) in 200 ml of toluene was added quickly at 20-25¡ãC. The reaction mixture was stirred for 3 hrs at the same temperature. After completion the reaction the mixture was poured into ice water and the toluene layer was separated. The aqueous layer was extracted again with toluene. The combined toluene phase was extracted with 200moi 20percent aqueous acetic acid (40ml acetic acid and 160ml water). The aq. acid extract was cooled to 5-10¡ãC and the pH was adjusted to basic using liquor ammonia (85ml) at 5-10¡ãC and extracted with toluene 3x300m1. The toluene layer was washed with water and dried over anhydrous sodium sulphate. The toluene layer was treated with carbon (10g) and filtered. The filtrate toluene is subjected to salt formation as per following methods.; Example-2) Process for the preparation of citalopram (by double Grignard method): A solution of 4-fluorophenyl magnesium bromides prepared from 153. 33g 4-flour bromobenzene (0.876 moles) and 25.33g magnesium turnings (1. 055 moles) and iodine (0.05gm) in dry 300mi tetrahydrofuran was added to a suspension of 100g 5- cyanophthalide (0.628 moles) in 900ml dry methylene dichloride at-4 to-2¡ãC. After the completion of the reaction a solution of 3-N, N dimethylaminopropyl magnesiumchloride in toluen/THF mixture [generated in situ by reacting 175g 3-N, N dimethylamiopropyl chloride (1. 446mole) in 350ml toluene with 41. 6gm magnesium turnings (9. 733moles) and iodine (0. 05g) in dry 75ml tetrahydrofuran and dibromoethane] was added between 0- 5¡ãC. The reaction mass was then maintained at-5 to 0¡ãC for 3-4 hours. After completion of the reaction, the reaction mass was quenched with 200ml 20percent aqueous ammonium chloride solution. The toluene layer was separated and washed with 200ml water. Methylene dichloride and THF was distilled. 189g sulphuric acid and 60ml of water was added to the toluene layer and heated to 85-90¡ãC. The same temperature was maintained for additional 4-5 hours. After completion of the reaction the reaction mass was diluted with 200ml water and the pH was adjusted to basic with liquor ammonia below 10-15¡ãC. The toluene layer was separated, washed with 200moi water and extracted with 400ml 20percent acetic acid (80mi acetic acid and 320ml water). The aq. acid extract was cooled to 5- 10¡ãC and the pH was adjusted to 8.5 to 9.0 using liquor ammonia (85ml) at 5-10¡ãC and extracted with toluene 3x600m1. The toluene layer was washed with water, dried over anhydrous sodium sulphate. The dried toluene layer was treated with carbon (10g) and filtered. The filtrate toluene was subjected to salt formation in accordance with the following methods:
The synthetic route of 82104-74-3 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; JUBILANT ORGANOSYS LIMITED; WO2005/77927; (2005); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem