Methanol → HCID 54104472, compound

HRID 328388Notes

Reaction equation

HRID 328388 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[CH:14][C:15]([OH:17])=[O:16])[CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.CO.[N+](=[CH2:29])=[N-]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][N:13]=[CH:14][C:15]([O:17][CH3:29])=[O:16])[CH2:9][N:8]=[C:7]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 54532359HCID 54532359, compound

Product 1

HCID 54104472HCID 54104472, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 6.29 g. (0.017 mole) 7-chloro-2-[[1-carboxymethylene)hydrazino]-5-phenyl-3H-1,4-benzodiazepine, methanol solvate, in 300 ml. of methylene chloride is slowly added an ethereal solution of diazomethane (9.27 ml., 0.22 mole) under nitrogen, at ambient temperature. After an hour, the solvent is removed in vacuo and the residue is recrystallized from ethyl acetate to give 3.20 g. of 7-chloro-2-[[1-(methoxycarbonyl)methylene]hydrazino]-5-phenyl-3H-1,4benzodizepine. The analytical sample is recrystallized from ethyl acetate-hexane.

Workup

  1. additionTo a stirred suspension of 6.29 g
  2. customat ambient temperature
  3. waitAfter an hour
  4. customthe solvent is removed in vacuo
  5. customthe residue is recrystallized from ethyl acetate
  6. customto give 3.20 g
  7. customThe analytical sample is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-947b15c8f3e9402b8f022b9b94e795e5
Source dataset
uspto-grants-1977_04
Patent number
US04017492

Reaction notes

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