Water → HCID 19025388, compound

HRID 1911093Notes

Reaction equation

HRID 1911093 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.O.[C:11](Cl)(Cl)=[S:12]>C(Cl)Cl>[I:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:11]=[S:12])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10040ThiophosgeneHCID 832214-Iodo-o-toluidine

Product 1

HCID 19025388HCID 19025388, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stifling solution of 4-iodo-2-methylaniline (1.0 g, 4.2 mmol) in DCM (50 mL) was added water (20 mL) followed by thiophosgene (490 mg, 4.2 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 (1.05 g, 89%). δH (CDCl3) 7.75 (1H, d, J 1.2 Hz), 7.62 (1H, dd, J 1.2, 8.3 Hz), 7.15 (1H, d, J 8.3 Hz), 2.20 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-244a8cda87cf46ad945372be8e01f00b
Source dataset
uspto-grants-2013_12
Patent number
US08604051B2

Reaction notes

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