Thiophosgene → HCID 58042234, compound

HRID 1911088Notes

Reaction equation

HRID 1911088 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-4824b50bc1324e528883ca68e12f6259
Source dataset
uspto-grants-2013_12
Patent number
US08604051B2

Reaction notes

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