4-Chlorophenyl Isocyanate → 3-(3-p-Chlorophenylureido)aniline

HRID 2398196Notes

Reaction equation

HRID 2398196 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]=[C:17]=[O:18])=[CH:12][CH:11]=1>C(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:18])[NH:7][C:3]2[CH:2]=[C:1]([CH:6]=[CH:5][CH:4]=2)[NH2:8])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 7935M-Phenylenediamine

Product 1

HCID 283743393-(3-p-Chlorophenylureido)aniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Phenylenediamine (10.8 g.) is dissolved in methylene chloride (500 ml.) at room temperature and a solution of p-chlorophenyl isocyanate (15.35 g.) in methylene chloride (50 ml.) is added dropwise with vigorous stirring. The mixture is stirred for 2 hours after the addition is complete, and the product is filtered off, washed with methylene chloride and dried. This solid thus obtained is crystallized from methanol (3 1.) to give 3-(3-p-chlorophenylureido)aniline, which slowly decomposes on heating to 310° C. without melting, but is analytically pure.

Workup

  1. additionafter the addition
  2. filtrationthe product is filtered off
  3. washwashed with methylene chloride
  4. customdried
  5. customThis solid thus obtained
  6. customis crystallized from methanol (3 1.)

Sources & evidence

ORD record
ord-4f1d6b9f72e1417f9b5425a43f3d8af1
Source dataset
uspto-grants-1977_05
Patent number
US04024183

Reaction notes

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