Water → HCID 53675857, compound

HRID 2166315Notes

Reaction equation

HRID 2166315 reaction equation
[CH3:1][C:2]([CH3:10])([CH:6]=[CH:7][S:8][CH3:9])[C:3](O)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.O>C(OCC)(=O)C>[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:3](=[O:4])[C:2]([CH3:10])([CH3:1])[CH:6]=[CH:7][S:8][CH3:9])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78124-ChloroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 54141775HCID 54141775, compound

Product 1

HCID 53675857HCID 53675857, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.5 g of 2,2-dimethyl-4-methylthio-3-butenoic acid in 20 mL of ethyl acetate was treated with 0.6 g of carbonyldiimidazole, and the solution was heated for 10 minutes at reflux. After the solution had cooled, 0.65 g of p-chloroaniline was added and heating continued for 16 hours. The solution was then cooled, poured into water and extracted into ethyl acetate. The organic layer was washed with 50 mL of 1N HCl, dried over MgSO4, and concentrated. The residual solid was recrystallized from CHCl3 /hexane to give 0.27 g of N-(4-chlorophenyl)-2,2-dimethyl-4-(methylthio)-3-butenamide, m.p. 105°-106° C.

Workup

  1. temperaturethe solution was heated for 10 minutes
  2. temperatureat reflux
  3. temperatureAfter the solution had cooled
  4. temperatureheating
  5. temperatureThe solution was then cooled
  6. extractionextracted into ethyl acetate
  7. washThe organic layer was washed with 50 mL of 1N HCl
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residual solid was recrystallized from CHCl3 /hexane

Sources & evidence

ORD record
ord-823c94e132ad444ea1bfb82d4ac0a400
Source dataset
uspto-grants-1990_07
Patent number
US04944795

Reaction notes

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