Dimethylamine → N-(4-methoxycarbonylamino-2-nitrophenyl)-2-dimethylaminoacetamide

HRID 1415649Notes

Reaction equation

HRID 1415649 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:16])[CH2:14]Br)=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=1)=[O:4].[CH3:20][NH:21][CH3:22]>C(O)C>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:16])[CH2:14][N:21]([CH3:22])[CH3:20])=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 21483050N-(4-methoxycarbonylamino-2-nitrophenyl)-2-bromoacetamide

Product 1

HCID 21483074N-(4-methoxycarbonylamino-2-nitrophenyl)-2-dimethylaminoacetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N-(4-methoxycarbonylamino-2-nitrophenyl)-2-bromoacetamide (25 g) in ethanol (250 ml) was treated with a solution of dimethylamine in ethanol (35.5 g of a 30% w/w solution) and the mixture refluxed for one hour. The ethanol was evaporated and the residual solid shaken with water and filtered to give N-(4-methoxycarbonylamino-2-nitrophenyl)-2-dimethylaminoacetamide (21.1 g), m.p. 186°-189° C.

Workup

  1. temperaturerefluxed for one hour
  2. customThe ethanol was evaporated
  3. filtrationfiltered

Sources & evidence

ORD record
ord-420ed934046143fc8baee747c635ed33
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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