Thiophosgene → HCID 58042234, compound

HRID 2061452Notes

Reaction equation

HRID 2061452 reaction equation
[C:1](Cl)(Cl)=[S:2].[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1[NH2:8]>C(Cl)(Cl)Cl.O>[F:5][C:6]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:7]=1[N:8]=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 58042234HCID 58042234, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Thiophosgene (3.55 mL, 46.4 mmol) was added to a rapidly-stirred mixture of 2-fluoro-4-iodoaniline (10.0 g, 42.2 mmol) in CHCl3 (200 mL) and water (100 mL). The mixture was stirred at r.t. for 16 h. The organic phase was dried (Na2SO4) and concentrated in vacuo to give the title compound as an off-white crystalline solid (11.8 g, quant.). δH (DMSO-d6) 7.87 (1H, dd, J 1.8, 9.5 Hz), 7.63 (1H, ddd, J 1.0, 1.8, 8.4 Hz), 7.25 (1H, dd, J 8.2, 8.4 Hz).

Workup

  1. dry with materialThe organic phase was dried (Na2SO4)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3915aa02b9a4764adc21974854f9dc6
Source dataset
uspto-grants-2012_10
Patent number
US08283359B2

Reaction notes

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