N-(2,6-Dichlorophenyl)thiourea → 1,3-Dichloro-2-isothiocyanatobenzene

HRID 839618

Reaction equation

HRID 839618 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](N)=[S:11]>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]=[S:11]

Participants

3

Reactant 1

HCID 722776N-(2,6-Dichlorophenyl)thiourea

Product 1

HCID 1232391,3-Dichloro-2-isothiocyanatobenzene

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 156.9 g. of 1-(2,6-dichlorophenyl)thiourea in 1 1. of chlorobenzene was refluxed for 20 hours and concentrated. The resulting oil was triturated with 1 1. of hot hexane which was filtered. On cooling overnight, 52 g. (36%) of 2,6-dichlorophenylisothiocyanate, m.p. 41°-42° separated. Concentration of the filtrate gave an additional 64.2 g. (44%), m.p. 41°-43° in two crops. Recrystallization of a sample from hexane gave the analytical sample, m.p. 41°-42°.

Workup

  1. concentrationconcentrated
  2. customThe resulting oil was triturated with 1 1
  3. filtrationof hot hexane which was filtered
  4. temperatureOn cooling overnight
  5. custom(36%) of 2,6-dichlorophenylisothiocyanate, m.p. 41°-42° separated
  6. customConcentration of the filtrate gave an additional 64.2 g
  7. customRecrystallization of a sample from hexane
  8. customgave the analytical sample, m.p. 41°-42°

Sources & evidence

ORD record
ord-4be22ed253f44506bb5a1aa5dc573405
Source dataset
uspto-grants-1978_06
Patent number
US04096276

Linked notes

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