Thiophosgene → HCID 2735551, compound

HRID 1628526Notes

Reaction equation

HRID 1628526 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([Cl:9])[CH:3]=1.[C:10](Cl)(Cl)=[S:11]>O1CCCC1.C(=O)([O-])O.[Na+]>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:10]=[S:11])=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 6101694-Bromo-2-chloroaniline

Product 1

HCID 2735551HCID 2735551, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 4-bromo-2-chloroaniline (30.0 g, 0.145 mol) in tetrahydrofuran (150 mL) and aqueous saturated sodium hydrogen carbonate (150 mL) was added thiophosgene (13.3 mL, 0.174 mol) at 0° C. The reaction mixture was stirred at room temperature for 1 hr. The mixture was extracted with ethyl acetate (×3). The combined organic layer was washed with brine (×1), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with cold-n-hexane to give the title compound as a colorless solid (25.51 g, 0.103 mol, 71%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (×3)
  2. washThe combined organic layer was washed with brine (×1)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with cold-n-hexane

Sources & evidence

ORD record
ord-746fbe5309ee48c4b98658242c5d742a
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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