4-Chloro-2-toluidine → N-(2-chloroethyl) N'-(4-chloro2-methylphenyl)urea

HRID 1439461Notes

Reaction equation

HRID 1439461 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]=[C:5]=[O:6].[Cl:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([CH3:15])[CH:9]=1>CCOCC>[Cl:1][CH2:2][CH2:3][NH:4][C:5]([NH:12][C:11]1[CH:13]=[CH:14][C:8]([Cl:7])=[CH:9][C:10]=1[CH3:15])=[O:6]

Participants

4

Reactant 2

HCID 72514-Chloro-2-toluidineHCID 160352-Chloroethyl isocyanate

Product 1

HCID 44721286N-(2-chloroethyl) N'-(4-chloro2-methylphenyl)urea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-chloroethyl isocyanate, 28.3 g. (0.27 mole) in 100 ml. of ether is added dropwise to a solution of 4-chloro-2-methylaniline, 38.0 g. (0.27 mole), in 500 ml. of ether. The solution is stirred 16 hours at room temperature, and the solid product is filtered and air dried, giving 47.2 g. (71% of theory) of the desired product, m.p. 190°.

Workup

  1. filtrationthe solid product is filtered
  2. customair dried
  3. customgiving 47.2 g

Sources & evidence

ORD record
ord-575bc220f00a4d29b86f67b25fd3e617
Source dataset
uspto-grants-1977_11
Patent number
US04059697

Reaction notes

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