Ammonia → HCID 86743359, compound

HRID 1606961Notes

Reaction equation

HRID 1606961 reaction equation
[Cl-].[Cl:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[Cl:25][C:26]1[C:31]2[C:32](=[O:44])[N:33]3[CH2:43][CH2:42][C@H:34]3[C:35]3[N:36]([CH:37]=[N:38][C:39]=3[CH:40]=O)[C:30]=2[CH:29]=[CH:28][CH:27]=1.N>O1CCCC1>[Cl:25][C:26]1[C:31]2[C:32](=[O:44])[N:33]3[CH2:43][CH2:42][C@H:34]3[C:35]3[N:36]([CH:37]=[N:38][C:39]=3/[CH:40]=[CH:3]\[Cl:2])[C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24533Sodium amideHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 53858665HCID 53858665, compound

Product 1

HCID 86743359HCID 86743359, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.5 g of an equimolar mixture of chloromethyltriphenylphosphonium chloride and sodium amide was stirred for 15 minutes in 100 ml of tetrahydrofuran, whereby the temperature rose to 33°. 11.1 g (38.58 mmol) of (S)-8-chloro-12,12a-dihydro-9-oxo-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxaldehyde was then added portionwise thereto, whereby the temperature rose to 45° with the evolution of ammonia. The mixture was stirred at room temperature for a further 1 hour, filtered and the filtrate was evaporated. After chromatography on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and subsequent recrystallization from ethyl acetate there was obtained (S)-8-chloro-1-[(Z)-2-chlorovinyl]-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of melting point 189°-191°.

Workup

  1. customrose to 33°
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. washAfter chromatography on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) and subsequent recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b026314bb201409ab647b7ce93257519
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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