Isopropyl Isothiocyanate → 1-(3-Isopropylthioureido)-3-(3-p-chlorophenylureido)benzene

HRID 2398197Notes

Reaction equation

HRID 2398197 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[NH:10][C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])=[CH:4][CH:3]=1.[CH:19]([N:22]=[C:23]=[S:24])([CH3:21])[CH3:20]>N1C=CC=CC=1>[CH:19]([NH:22][C:23](=[S:24])[NH:14][C:13]1[CH:15]=[CH:16][CH:17]=[C:11]([NH:10][C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:18])[CH:12]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 75263Isopropyl IsothiocyanateHCID 283743393-(3-p-Chlorophenylureido)aniline

Product 1

HCID 538688891-(3-Isopropylthioureido)-3-(3-p-chlorophenylureido)benzene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(3-p-chlorophenylureido)aniline (2.0 g.) in pyridine (40 ml.) is stirred at 0° C. with isopropyl isothiocyanate (0.77 ml.). The solution is allowed to warm slowly to room temperature and is stirred for 48 hours. The solution is filtered, the pyridine is removed by distillation under reduced pressure and the residue is crystallized from methanol (300 ml.) to give 1-(3-isopropylthioureido)-3-(3-p-chlorophenylureido)benzene, m.p. 197°-198° C. with decomposition.

Workup

  1. filtrationThe solution is filtered
  2. customthe pyridine is removed by distillation under reduced pressure
  3. customthe residue is crystallized from methanol (300 ml.)

Sources & evidence

ORD record
ord-70ef54ad138840968a864c33ee3a0399
Source dataset
uspto-grants-1977_05
Patent number
US04024183

Reaction notes

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