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

HRID 854697Notes

Reaction equation

HRID 854697 reaction equation
[F:1][S:2]([F:17])([F:16])([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](O)=[O:12])=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[NH3:24]>O1CCCC1.CN(C)C=O>[F:1][S:2]([F:17])([F:16])([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([NH2:24])=[O:12])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 740695713-(4-Pentafluorosulfanyl-phenyl)-acrylic Acid

Product 1

HCID 865985163-(4-Pentafluorosulfanyl-phenyl)-acrylamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 5.70 g (20.8 mmol) 3-(4-pentafluorosulfanyl-phenyl)-acrylic acid in 30 ml tetrahydrofuran and 0.21 ml N,N-dimethyl formamide a solution of 3.47 ml (27.4 mmol) oxalyl chloride in 5.0 ml tetrahydrofuran was added dropwise at 0° C. within 10 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 mixture of 300 ml ice and 120 ml of a 25% aqueous ammonia solution. The precipitated amide was collected, washed with water and n-heptane and dried at 40° C. in vacuo. Yield 5.17 g (91%) 3-(4-pentafluorosulfanyl-phenyl)-acrylamide.

Workup

  1. additionwas added dropwise at 0° C. within 10 min
  2. customThe precipitated amide was collected
  3. washwashed with water and n-heptane
  4. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-6d2dede815b147deb5c79087ebe32e60
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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