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

HRID 2061458Notes

Reaction equation

HRID 2061458 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-24f5b980d46d49949a016d4f7699132d
Source dataset
uspto-grants-2012_10
Patent number
US08283359B2

Reaction notes

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