p-Toluohydrazide → 1-Methyl-3-[(4-methylbenzoyl)amino]urea

HRID 660846Notes

Reaction equation

HRID 660846 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.[CH3:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([NH:31][NH2:32])=[O:30])=[CH:27][CH:26]=1>ClCCl>[CH3:1][NH:2][C:3]([NH:32][NH:31][C:29](=[O:30])[C:28]1[CH:27]=[CH:26][C:25]([CH3:24])=[CH:34][CH:33]=1)=[O:4]

Participants

5

Reactant 3

HCID 77174p-ToluohydrazideHCID 79892Carbamic acid, N-methyl-, 4-nitrophenyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 32718701-Methyl-3-[(4-methylbenzoyl)amino]urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

653 mg (3.33 mmol) of 4-nitrophenyl methylcarbamate and 473 mg (3.22 mmol) of N,N-diisopropylethylamine are added to 500 mg (3.33 mmol) of 4-methylbenzoic acid hydrazide in 15 ml dichloromethane and the mixture stirred overnight at room temperature. The precipitate formed is recovered by filtration, washed with diethyl ether and dried in vacuo. 602 mg (87% of theory) of the target compound are thus obtained.

Workup

  1. customThe precipitate formed
  2. filtrationis recovered by filtration
  3. washwashed with diethyl ether
  4. customdried in vacuo
  5. custom602 mg (87% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-6b5361132a2e41c3816495284ebab3d1
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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