Dimethylformamide → HCID 90693962, compound

HRID 2375445Notes

Reaction equation

HRID 2375445 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CN(C=O)C.[CH3:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[CH2:21]1[CH:28]([C:29](Cl)=[O:30])[CH2:27][CH2:26][S:23](=[O:25])(=[O:24])[CH2:22]1>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C.O>[O:24]=[S:23]1(=[O:25])[CH2:26][CH2:27][CH:28]([C:29]([N:18]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:17]2[CH:19]=[CH:20][C:14]([CH3:13])=[CH:15][CH:16]=2)=[O:30])[CH2:21][CH2:22]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 7813p-ToluidineHCID 22397852HCID 22397852, compound

Product 1

HCID 90693962HCID 90693962, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carboxylate and ethyl bromoacetate were added to a DMF solution of 4-methylaniline and heated while stirring. The reaction mixture was added with water and ethyl acetate. After the organic layer was separated, washed and dried, the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was dissolved in methylene chloride, and pyridine, tetrahydro-2H-thiopyrane-4-carbonyl chloride 1,1-dioxide were added to the resulting solution and stirred. After the reaction solution was concentrated, 1M hydrochloric acid and chloroform were added. The organic layer separated was washed and dried and the solvent was evaporated under reduced pressure. The resulting crude product was purified with a silica gel column chromatography to obtain ethyl ([(1,1-dioxotetrahydro-2H-thiopyran-4-yl)carbonyl](4-methylphenyl)amino)acetate (colorless oily product). FAB-MS [(M+H)+]: 354.

Workup

  1. temperatureheated
  2. customAfter the organic layer was separated
  3. washwashed
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customto obtain a crude product
  7. stirringstirred
  8. concentrationAfter the reaction solution was concentrated
  9. addition1M hydrochloric acid and chloroform were added
  10. customThe organic layer separated
  11. washwas washed
  12. customdried
  13. customthe solvent was evaporated under reduced pressure
  14. customThe resulting crude product was purified with a silica gel column chromatography

Sources & evidence

ORD record
ord-d732dfab4a1f49b29fbd83a61c68fec5
Source dataset
uspto-grants-2008_12
Patent number
US07465748B2

Reaction notes

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