Tetrahydrofuran → HCID 86743357, compound

HRID 1606958Notes

Reaction equation

HRID 1606958 reaction equation
[Cl-].[Cl:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[F:25][C:26]1[CH:27]=[CH:28][C:29]2[N:35]3[CH:36]=[N:37][C:38]([CH:39]=O)=[C:34]3[CH2:33][N:32]([CH3:41])[C:31](=O)[C:30]=2[CH:43]=1.[O:44]1CCCC1>>[Cl:2]/[CH:3]=[CH:39]\[C:38]1[NH:37][C:36](=[O:44])[N:35]2[C:29]3[CH:28]=[CH:27][C:26]([F:25])=[CH:43][C:30]=3[CH2:31][N:32]([CH3:41])[CH2:33][C:34]=12

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24533Sodium amideHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 198515378-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

Product 1

HCID 86743357HCID 86743357, compound

Procedure

25 g of an equimolar mixture of chloromethyltriphenylphosphonium chloride and sodium amide was stirred at room temperature in 120 ml of tetrahydrofuran for 20 minutes. 12.9 g (50 mmol) of 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde was then added thereto and the mixture was stirred at room temperature for 1 hour and at the boiling temperature for 10 minutes. The mixture was cooled, filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and recrystallization from acetonitrile there was obtained 3-[(Z)-2-chlorovinyl]-8-fluoro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepine-one of melting point 220°-221°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. washAfter chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-680c627b99a44d5888ee9dbef89c0c87
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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