Ammonia → 3-(4-Trifluoromethylsulfanyl-phenyl)-acrylamide

HRID 2113871Notes

Reaction equation

HRID 2113871 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=O)=[CH:8][CH:7]=1)([F:4])[F:3].C(Cl)(=O)C(Cl)=O.[NH3:23]>O1CCCC1.CN(C)C=O>[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([NH2:23])=[O:16])=[CH:8][CH:7]=1)([F:4])[F:3]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 533956353-{4-[(Trifluoromethyl)sulfanyl]phenyl}prop-2-enoic acid

Product 1

HCID 691120573-(4-Trifluoromethylsulfanyl-phenyl)-acrylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 5.24 g (21.1 mmol) 3-(4-trifluoromethylsulfanyl-phenyl)-acrylic acid in 30.0 ml tetrahydrofuran and 0.3 ml N,N-dimethylformamide a solution of 2.70 ml (32.0 mmol) oxalyl chloride in 5.0 ml tetrahydrofuran was added dropwise at 0° C. within 20 min. Stirring was continued at 0-5° C. for 30 min. and 3 h at room temperature thereafter. The resulting solution was cooled to 0-5° C. again and then added within 15 min. to 100 ml of a 25% aqueous ammonia solution. After evaporation of the organic solvent, 200 ml water were added and the solution cooled. The precipitated amide was collected, washed with water and dried at 40° C. in vacuo. Yield 4.62 g (89%) 3-(4-Trifluoromethylsulfanyl-phenyl)-acrylamide.

Workup

  1. additionwas added dropwise at 0° C. within 20 min
  2. customAfter evaporation of the organic solvent, 200 ml water
  3. additionwere added
  4. temperaturethe solution cooled
  5. customThe precipitated amide was collected
  6. washwashed with water
  7. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-285b7ee0832c44fabc0d755dc07bcecb
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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