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

HRID 1639466ノート

反応式

HRID 1639466 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8088999de7e14282bb0914eb6c4306ef
出典データセット
uspto-grants-1989_11
特許番号
US04883914

反応ノート

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