Water → 11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2351377Notes

Reaction equation

HRID 2351377 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[NH:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17](Cl)([Cl:19])=[O:18].O>O1CCOCC1.C1(C)C=CC=CC=1>[Cl:19][C:17]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[NH:11][C:5]2[CH:4]=[CH:3][CH:2]=[N:1][C:6]1=2)=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 6371PhosgeneHCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

Product 1

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 158.3 g (0.75 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one in 3 liters of dioxane, 730 ml (1.46 mol) of a 20% solution of phosgene in toluene was added dropwise within 45 minutes and the resulting mixture was then stirred for 2 hours at ambient temperature. 1.5 l of water were added, the mixture was stirred for a further 2 hours at ambient temperature and the precipitate formed was suction filtered. The product was washed thoroughly with water and dried in a circulating air dryer. Colourless crystals, m.p. 239°-240° C.

Workup

  1. additionwas added dropwise within 45 minutes
  2. stirringthe mixture was stirred for a further 2 hours at ambient temperature
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washThe product was washed thoroughly with water
  6. customdried in a circulating air dryer

Sources & evidence

ORD record
ord-367d288ebc9b4a64b10b9ad7cbabc1dc
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

Loading…