Ammonia → HCID 67012321, compound

HRID 750982Notes

Reaction equation

HRID 750982 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[NH3:20]>O1CCCC1.CN(C)C=O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([NH2:20])=[O:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 6065043-[4-(methylsulfanyl)phenyl]acrylic acid

Product 1

HCID 67012321HCID 67012321, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 5.00 g (25.7 mmol) 3-(4-methylsulfanyl-phenyl)-acrylic acid in 30.0 ml tetrahydrofuran and 0.3 ml N,N-dimethyl formamide a solution of 4.90 ml (38.6 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 n-heptane and dried at 40° C. in vacuo. Yield 4.46 g (90%) 3-(4-methylsulfanyl-phenyl)-acrylamide as an off-white solid melting at 193° C.

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 and n-heptane
  7. customdried at 40° C. in vacuo

Sources & evidence

ORD record
ord-d247535506a845cfaf0a30f1250512e6
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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