Thionyl Chloride → 4-Amino-3-chloro-5-(trifluoromethyl)benzoyl chloride

HRID 11898Notes

Reaction equation

HRID 11898 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:15].S(Cl)([Cl:18])=O>>[Cl:15][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:2]=1[NH2:1])[C:6]([Cl:18])=[O:7]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 46435494-amino-3-chloro-5-(trifluoromethyl)benzoic Acid

Product 1

HCID 133555094-Amino-3-chloro-5-(trifluoromethyl)benzoyl chlorideYield 80%

Procedure

13 g (0.0543 mol) of 4-amino-3-chloro-5-trifluoromethyl-benzoic acid was added to 32.5 ml of thionyl chloride. The suspension was heated until the crystals have dissolved, then refluxing was continued for another 2 h. After cooling to room temperature, the remaining thionyl chloride was evaporated under reduced pressure, thus obtained crude 3-chloro-4-amino-5-trifluoromethyl-benzoyl chloride, which was dissolved in chloroform at heating. Filtered with heating and evaporated under reduced pressure to remove chloroform, obtained the subject product. Yield: 80–90%, melting point: 110–115° C.

Workup

  1. temperatureThe suspension was heated until the crystals
  2. dissolutionhave dissolved
  3. temperaturerefluxing
  4. customthe remaining thionyl chloride was evaporated under reduced pressure

Sources & evidence

ORD record
ord-37c79427ac8147a1b820d04799e1fa3a
Source dataset
uspto-grants-2006_08
Patent number
US07098364B2

Reaction notes

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