4-Chlorobenzohydrazide → 2-(4-chlorobenzoyl)-N-methylhydrazinecarboxamide

HRID 660845Notes

Reaction equation

HRID 660845 reaction equation
[CH3:1][NH:2][C:3](=O)[O:4]C1C=CC([N+]([O-])=O)=CC=1.C(N(CC)C(C)C)(C)C.[Cl:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=1>ClCCl>[Cl:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH:32][C:3]([NH:2][CH3:1])=[O:4])=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 108164-ChlorobenzohydrazideHCID 79892Carbamic acid, N-methyl-, 4-nitrophenyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 3116972-(4-chlorobenzoyl)-N-methylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

575 mg (2.93 mmol) of 4-nitrophenyl methylcarbamate and 417 mg (3.22 mmol) of N,N-diisopropylethylamine are successively added to 500 mg (2.93 mmol) of 4-chlorobenzoic acid hydrazide in 15 ml dichloromethane and the mixture stirred overnight at room temperature. It is concentrated, the residue is purified by preparative HPLC [Method 9] and 410 mg (61% of theory) of the target compound are thus obtained.

Workup

  1. concentrationIt is concentrated
  2. customthe residue is purified by preparative HPLC [Method 9] and 410 mg (61% of theory) of the target compound
  3. customare thus obtained

Sources & evidence

ORD record
ord-06d0fcd864f944228a002254fc4aa65d
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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