Pyridine → 5-Methyl-4-(dimethylaminomethyl)-2-thiophenemethanol N,N,3-trimethyl-3-thiophene carboxamide

HRID 867924

반응식

HRID 867924 반응식
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=O.[C:10](Cl)(=O)[C:11](Cl)=[O:12].[N:16]1[CH:21]=CC=C[CH:17]=1>C1(C)C=CC=CC=1>[CH3:17][N:16]([CH3:21])[C:7]([C:6]1([CH3:10])[CH:5]=[CH:4][S:3][CH2:2]1)=[O:9].[CH3:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[CH:5][C:6]=1[CH2:7][N:16]([CH3:21])[CH3:17]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 46254092-Methylthiophene-3-carboxylic acid

생성물 1

HCID 704178535-Methyl-4-(dimethylaminomethyl)-2-thiophenemethanol N,N,3-trimethyl-3-thiophene carboxamide

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-methyl-3-thiophene carboxylic acid (2 g) and oxalyl chloride (2 ml) in dry toluene (20 ml) was heated under reflux and was treated with pyridine (0.05 ml). The reaction mixture was heated at reflux for 1 h, cooled and partially evaporated. The residue was added to a solution of dimethylamine in toluene at 0° to 5° C. After 2 hours water and diethyl ether were added. The organic phase was washed with dilute hydrochloric acid, sodium hydroxide and water, dried and evaporated to an oil which was distilled to give the title compound (1.4 g) as a colourless oil b.p. 100°/0.1 mm.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 1 h
  5. temperaturecooled
  6. custompartially evaporated
  7. additionThe residue was added to a solution of dimethylamine in toluene at 0° to 5° C
  8. additionAfter 2 hours water and diethyl ether were added
  9. washThe organic phase was washed with dilute hydrochloric acid, sodium hydroxide and water
  10. customdried
  11. customevaporated to an oil which
  12. distillationwas distilled

출처 및 근거

ORD 기록
ord-0972fc1dee8f463893848b08825a9a52
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04777179

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