Methyl isothiocyanate → Thiourea, N-(2,6-dichlorophenyl)-N'-methyl-

HRID 596650Notes

Reaction equation

HRID 596650 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:3]=1[NH2:4].[CH3:10][N:11]=[C:12]=[S:13]>C(O)C>[CH3:10][NH:11][C:12]([NH:4][C:3]1[C:2]([Cl:1])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:9])=[S:13]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 118462,6-Dichloroaniline

Product 1

HCID 7942238Thiourea, N-(2,6-dichlorophenyl)-N'-methyl-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

130 g of 2,6-dichloro-aniline, 100 g of methyl isothiocyanate and 300 ml of 95% ethanol are refluxed during 14 hours, with stirring. The resulting solution is cooled in the freezer: the white solid formed is filtered and washed with isopropyl oxide. After recrystallization from isopropanol, 65 g of product (III : R = CH3), m.p. = 184° C, are collected.

Workup

  1. temperatureThe resulting solution is cooled in the freezer
  2. customthe white solid formed
  3. filtrationis filtered
  4. washwashed with isopropyl oxide
  5. customAfter recrystallization from isopropanol, 65 g of product (III : R = CH3), m.p. = 184° C
  6. customare collected

Sources & evidence

ORD record
ord-3971929cc6e24d77b53f34cdb3ed7ad5
Source dataset
uspto-grants-1977_03
Patent number
US04011342

Reaction notes

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