Water → HCID 19025388, compound

HRID 2061457Notes

Reaction equation

HRID 2061457 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 stirring 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-76b3233e57c94637bc72afa8d3ada1cd
Source dataset
uspto-grants-2012_10
Patent number
US08283359B2

Reaction notes

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