Sodium amide → 3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one

HRID 1606951Notes

Reaction equation

HRID 1606951 reaction equation
[Cl-].[Cl:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-].[Na+].[CH3:25][N:26]1[C:32](=[O:33])[C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[N:29]2[CH:38]=[N:39][C:40]([CH:41]=O)=[C:28]2[CH2:27]1>O1CCCC1>[Cl:2]/[CH:3]=[CH:41]\[C:40]1[N:39]=[CH:38][N:29]2[C:30]3[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=3[C:32](=[O:33])[N:26]([CH3:25])[CH2:27][C:28]=12

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 198330205,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

Product 1

HCID 867433543-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

13.50 g of an equimolar mixture of chloromethyltriphenylphosphonium chloride and sodium amide were stirred for 15 minutes with 50 ml of tetrahydrofuran, whereby the temperature rose to 42°. 6.2 g (25.7 mmol) of 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde were then added portionwise thereto, the mixture was stirred at room temperature for a further hour, filtered and the filtrate was evaporated. After chromatography of the residue on silica gel while eluting with cyclohexane/ether/isopropanol (3:3:1) there was obtained 3-[(Z)-2-chlorovinyl]-4,5-dihydro-5-methyl-6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one of melting point 197°-199°.

Workup

  1. customrose to 42°
  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) there

Sources & evidence

ORD record
ord-5636b61a550c457f9c91d4045d745702
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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