Phosgene → HCID 21414253, compound

HRID 442330Notes

Reaction equation

HRID 442330 reaction equation
[C:1]1([CH:7]2[C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[NH:11][C:10](=[O:19])[CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](Cl)([Cl:22])=[O:21]>C1C=CC=CC=1>[Cl:22][C:20]([N:8]1[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[NH:11][C:10](=[O:19])[CH2:9]1)=[O:21]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 157641-Demethyl-4,5-dihydrodiazepam

Product 1

HCID 21414253HCID 21414253, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

0.84 g. of dry, solid sodium hydrocarbonate are added to a suspension of 1.36 g. (5 mmoles) of 5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 60 ml. of absolute benzene, and 15 ml. of a 10% phosgene solution in benzene are added dropwise to the mixture at 10°-15° C. The mixture is stirred at 10°-15° C. for one hour and then at room temperature overnight. The inorganic salts are filtered off and washed with 50 ml. of acetone. The organic phase is evaporated, and the dry residue is recrystallized from benzene. 1.08 g. (64.5 %) of 4-chlorocarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 181°-184° C., Rf2 = 0.82.

Workup

  1. customof dry
  2. additionsolid sodium hydrocarbonate are added to a suspension of 1.36 g
  3. customat room temperature
  4. customovernight
  5. filtrationThe inorganic salts are filtered off
  6. washwashed with 50 ml
  7. customThe organic phase is evaporated
  8. customthe dry residue is recrystallized from benzene

Sources & evidence

ORD record
ord-d77dd05d62ff4016a54b2ccbea3b4312
Source dataset
uspto-grants-1977_08
Patent number
US04045433

Reaction notes

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