Dimethylformamide → 2-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide

HRID 1639466노트

반응식

HRID 1639466 반응식
[CH3:1][C:2]1[O:3][C:4](=[O:11])[C:5]([CH3:10])([CH:7]([CH3:9])[CH3:8])[N:6]=1.CN(C=O)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.[Na]>C1COCC1>[C:2]([NH:6][C:5]([CH3:10])([CH:7]([CH3:9])[CH3:8])[C:4]([NH:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:24])=[O:25])=[O:11])(=[O:3])[CH3:1]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 146957652,4-Dimethyl-4-isopropyl-2-oxazolin-5-oneHCID 66664522Sodium p-toluene sulfonamide

생성물 1

HCID 146246882-acetamido-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,4-Dimethyl-4-isopropyl-2-oxazolin-5-one (2.0 g) is mixed with DMF (50 mL), THF (70 mL) and sodium p-toluene sulfonamide (5.0 g), and the resulting mixture is heated at reflux for 16 hours. At the end of this time the mixture is cooled, and the solvents are removed under vacuum. The residue is mixed with water and the pH adjusted to 8 with NaHCO3. The aqueous mixture is extracted with ethyl acetate and the organic layers are discarded. The aqueous mixture is acidified to pH≈4 with HCl and saturated with NaCl and extracted with ethyl acetate. The organic extracts are combined, dried over MgSO4, filtered and evaporated to give 0.66 of the title product.

후처리

  1. temperaturethe resulting mixture is heated
  2. temperatureat reflux for 16 hours
  3. temperatureAt the end of this time the mixture is cooled
  4. customthe solvents are removed under vacuum
  5. additionThe residue is mixed with water
  6. extractionThe aqueous mixture is extracted with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-8088999de7e14282bb0914eb6c4306ef
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04883914

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