Phenyl isocyanate → 1-Hydroxy-1-(1-methylpropyl)-3-phenylurea

HRID 647249Notes

Reaction equation

HRID 647249 reaction equation
Cl.[CH:2]([NH:6][OH:7])([CH2:4][CH3:5])[CH3:3].C(=O)(O)[O-].[Na+].[C:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>COCCOC>[C:13]1([NH:19][C:20]([N:6]([CH:2]([CH2:4][CH3:5])[CH3:3])[OH:7])=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 516892Sodium BicarbonateHCID 12355451N-Hydroxy-sec-butylammonium chloride

Product 1

HCID 127707111-Hydroxy-1-(1-methylpropyl)-3-phenylurea

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 500 ml of ethylene glycol dimethyl ether, 209.1 g (1.5 moles) of 90% pure N-sec.-butylhydroxylamine hydrochloride and 151.2 g (1.8 moles) of sodium bicarbonate was stirred at room temperature for 1 hour and 178.5 g (1.5 moles) of phenyl isocyanate were then added at 0° to 5° C. The mixture was subsequently stirred at 10° C. for 1 hour, the salt was then filtered off and the filtrate was evaporated in vacuo. 310 g (99% of theory) of N-phenyl-N'-sec.-butyl-N'-hydroxyurea remained as a colourless powder with a melting point of 107° C.

Workup

  1. stirringThe mixture was subsequently stirred at 10° C. for 1 hour
  2. filtrationthe salt was then filtered off
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-79e5355da80341a987e8b82dac6d810c
Source dataset
uspto-grants-1983_10
Patent number
US04408055

Reaction notes

Loading…