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

HRID 1944063Notes

Reaction equation

HRID 1944063 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-0e2a8177ae994368a666e802eb2f6fd2
Source dataset
uspto-grants-2013_03
Patent number
US08394822B2

Reaction notes

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