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Ammonia → 2,3-Dichloro-6-(trifluoromethyl)benzamide

HRID 1005481
Notes
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Reaction equation

HRID 1005481 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.[NH3:20]>C1C=CC=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:3]=1[C:4]([NH2:20])=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 116518032,3-Dichloro-6-(trifluoromethyl)benzoic acid

Product 1

HCID 154569832,3-Dichloro-6-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241Benzene
Solvent

Conditions

Temperature
5 °C

Procedure

To a solution of 250 g of 2,3-dichloro-6-trifluoromethylbenzoic acid in 2 liters of benzene was added 5 drops of pyridine and 172 g of thionyl chloride and then the mixture was heated at reflux for 22 hours. After cooling down, the solution was concentrated under reduced pressure, and 2,3-dichloro-6-trifluoromethylbenzyl chloride obtained was added into 1 liter of 28% aqueous ammonia solution, which has been cooled down to 5° C. over 10 minutes with stirring. Then, the solution was further stirred for 1 hour at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and then with saturated saline solution, and was dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the crude crystals obtained were washed with n-hexane and then filtered to give 229 g of the title compound(mp. 118-20° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 22 hours
  3. temperatureAfter cooling down
  4. concentrationthe solution was concentrated under reduced pressure, and 2,3-dichloro-6-trifluoromethylbenzyl chloride
  5. customobtained
  6. stirringThen, the solution was further stirred for 1 hour at room temperature
  7. extractionThe reaction mixture was extracted with ethyl acetate
  8. washthe extract was washed with water
  9. dry with materialwith saturated saline solution, and was dried over anhydrous magnesium sulfate
  10. distillationThe solvent was distilled under reduced pressure
  11. customthe crude crystals obtained
  12. washwere washed with n-hexane
  13. filtrationfiltered

Sources & evidence

ORD record
ord-95de71d43eb2490e873cae9b9aeed6fb
Source dataset
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06054605

Reaction notes

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