Thiophosgene → HCID 58042234, compound

HRID 1944057Notes

Reaction equation

HRID 1944057 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-049a07b473d0481ea974ece43eeb9683
Source dataset
uspto-grants-2013_03
Patent number
US08394822B2

Reaction notes

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