Dimethylcarbamoyl Chloride → HCID 57255687, compound

HRID 1833833Notes

Reaction equation

HRID 1833833 reaction equation
[CH:1]([NH:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)([CH2:3][CH3:4])[CH3:2].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>N1C=CC=CC=1>[CH:1]([NH:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][C:18]([N:17]([CH3:21])[CH3:16])=[O:19])[CH:9]=1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 438312603-Amino-N-(1-methylpropyl)benzeneacetamide

Product 1

HCID 57255687HCID 57255687, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20.6 g (0.1 mol) of 3-amino-phenylacetic acid sec.-butylamide were dissolved in 100 ml of pyridine. 10.75 g (0.1 mol) of dimethylcarbamic acid chloride were added thereto. The mixture was stirred for a further 2 hours at room temperature and 2 hours at 50° to 60° C. The residue which remained after distilling off the pyridine under reduced pressure was stirred with very dilute hydrochloric acid, filtered off and then recrystallized from butyl acetate. 17 g (61.5% of theory) of 3-(N',N'-dimethylureido)-phenylacetic acid sec.-butylamide of melting point 170-171° C were obtained.

Workup

  1. distillationafter distilling off the pyridine under reduced pressure
  2. stirringwas stirred with very dilute hydrochloric acid
  3. filtrationfiltered off
  4. customrecrystallized from butyl acetate

Sources & evidence

ORD record
ord-e5e14ef6659a4f148c384e5e03a530de
Source dataset
uspto-grants-1978_01
Patent number
US04067726

Reaction notes

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