Water → 2-Chloro-4-iodo-1-isothiocyanatobenzene

HRID 1911094Notes

Reaction equation

HRID 1911094 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].O.[C:11](Cl)(Cl)=[S:12]>C(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[N:4]=[C:11]=[S:12]

Participants

5

Reactant 3

HCID 962WaterHCID 10040ThiophosgeneHCID 2829302-Chloro-4-iodoaniline

Product 1

HCID 866310502-Chloro-4-iodo-1-isothiocyanatobenzeneYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chloro-4-iodoaniline (1.0 g, 3.9 mmol) in DCM (50 mL) was added water (20 mL) followed by thiophosgene (476 mg, 4.1 mmol). The reaction mixture was stirred overnight before the layers were separated and the organic layer dried (Na2SO4) and evaporated in vacuo to give the desired product as a brown solid (1.0 g, 86%). δH (CDCl3) 7.79 (1H, d, J 1.9 Hz), 7.58 (1H, dd, J 1.9, 8.4 Hz), 6.97 (1H, d, J 8.4 Hz).

Workup

  1. customwere separated
  2. dry with materialthe organic layer dried (Na2SO4)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-479769a6a4bd42129a3946def1358656
Source dataset
uspto-grants-2013_12
Patent number
US08604051B2

Reaction notes

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