Ammonia → N-Cyclopentyl-N′-methylurea

HRID 1287262Notes

Reaction equation

HRID 1287262 reaction equation
CO[C:3](=O)[NH2:4].[CH:6]1(CN)[CH2:10][CH2:9][CH2:8][CH2:7]1.[NH3:13].[O:14]1[CH2:19]COCC1>>[CH:6]1([NH:13][C:19](=[O:14])[NH:4][CH3:3])[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 11722Methyl CarbamateHCID 312751,4-DioxaneHCID 80153Cyclopentanemethylamine

Product 1

HCID 13428331N-Cyclopentyl-N′-methylurea

Procedure

20.3 g of N-[4-(β-<2-methoxy-5-methyl-benzamido>-ethyl)-benzensulfonyl]-carbamic acid methyl ester (melting point 169° - 171° C) were dissolved in 100 ml of dioxane. After addition of 4.95 g of cyclopentylmethylamine, the whole was heated for 1 hour to the boiling temperature, under reflux. The clear solution was poured in a very diluted (about 0.25 %) aqueous ammonia solution, filtered with the use of charcoal and the filtrate was acidified with dilute hydrochloric acid. The N-[4-(β-<2-methoxy-5-methyl-benzamido>-ethyl)-benzenesulfonyl]-N'-cyclopentyl-methyl-urea obtained was filtered off with suction. After recrystallization from methanol, it was found to melt at 147° - 149° C.

Workup

  1. temperaturethe whole was heated for 1 hour to the boiling temperature
  2. temperatureunder reflux
  3. additionThe clear solution was poured in
  4. filtrationfiltered with the use of charcoal

Sources & evidence

ORD record
ord-f6f25663281c4397978e97e11e61b87c
Source dataset
uspto-grants-1976_10
Patent number
US03984416

Reaction notes

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