Methanol → Urea, 1-(2-chloroethyl)-3-(m-tolyl)-

HRID 80167Notes

Reaction equation

HRID 80167 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[C:7]1([CH3:14])[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[CH:8]=1.CO>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:13][C:9]1[CH:8]=[C:7]([CH3:14])[CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

6

Reactant 3

HCID 887MethanolHCID 7934m-ToluidineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 97216Urea, 1-(2-chloroethyl)-3-(m-tolyl)-Yield 95,753.203%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

1-Chloro-2-isocyanato-ethane (2.36 g, 0.02239 mmol) was added dropwise to a stirred solution of m-tolylamine (2 g, 0.01866 mmol) in toluene (50 mL) over a period of 30 minutes at 0° C. The reaction mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC (5% MeOH in DCM). The reaction mixture was filtered, washed with toluene and dried under reduced pressure to afford 3.8 g (97% yield) of 1-(2-chloro-ethyl)-3-m-tolyl-urea.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-2f2e5fb21917407d99994692c9499076
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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