Dichloromethane → Ethyl 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate

HRID 1973530Notes

Reaction equation

HRID 1973530 reaction equation
[C:1]([C:9]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:10]=1[NH:11][C:12](=[O:21])[C:13](=[N:19]O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>[Zn].C(O)(=O)C>[Cl:26][C:24]1[CH:23]=[CH:22][C:10]2[NH:11][C:12](=[O:21])[CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:19]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:9]=2[CH:25]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 86733591Ethyl 2'-benzoyl-4'-chloro-mesoxalanilate 2-oxime

Product 1

HCID 110682Ethyl 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2 g. of ethyl 2'-benzoyl-4'-chloro-mesoxalanilate 2-oxime in 40 ml. of methylene chloride is treated with 2 g. of zinc dust. 4 ml. of glacial acetic acid are added dropwise within 5 minutes with stirring. After the addition, the mixture is stirred at room temperature for 1 hour. The reaction mixture is filtered and the filtrate evaporated. The residue is boiled under reflux for 2 hours in 20 ml. of benzene and 2 ml. of glacial acetic acid. The reaction mixture is washed out with 10% soda solution, dried over sodium sulphate and evaporated. Crystallization of the residue from alcohol yields ethyl 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one-3-carboxylate, m.p. 232°-234°. Further material crystallizes from the mother liquor.

Workup

  1. additionAfter the addition
  2. stirringthe mixture is stirred at room temperature for 1 hour
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate evaporated
  5. temperatureunder reflux for 2 hours in 20 ml
  6. washThe reaction mixture is washed out with 10% soda solution
  7. dry with materialdried over sodium sulphate
  8. customevaporated
  9. customCrystallization of the residue from alcohol

Sources & evidence

ORD record
ord-c2012fdb8b3a4bc89d8c0f94f0e0f1ec
Source dataset
uspto-grants-1976_12
Patent number
US03997591

Reaction notes

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