Chloroform → Ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate

HRID 1066228노트

반응식

HRID 1066228 반응식
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]2[CH2:13][CH2:14][CH2:15][C:16](=[O:17])[C:4]=12.P(Cl)(Cl)(Cl)=O.[CH:23]([Cl:26])(Cl)Cl>CN(C)C=O>[Cl:26][C:23]1[C:4]2[C:5](=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[S:7][C:3]=2[S:2][CH3:1])[CH2:13][CH2:14][C:15]=1[CH:16]=[O:17]

참가 물질

5

반응물 3

HCID 6212ChloroformHCID 24813Phosphorus oxychlorideHCID 2778748Ethyl 3-(methylthio)-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

생성물 1

HCID 2778781Ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate수율 73.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl 4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (5.47 g) was dissolved in chloroform (130 ml) and added dropwise to a solution of phosphorus oxychloride (50.71 g) in N,N-dimethylformamide (40 ml) at 0° C. This mixture was stirred at room temperature, after which it was refluxed under heating in a nitrogen stream for 4.5 hours. The reaction mixture was poured over ice water and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off to yield ethyl 4-chloro-5-formyl-6,7-dihydro-3-methylthiobenzo[c]thiophene-1-carboxylate (4.72 g, 73.8%), which was then recrystallized from ethyl acetate. Yellow prisms. Melting point 79-80° C.

후처리

  1. temperatureafter which it was refluxed
  2. temperatureunder heating in a nitrogen stream for 4.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationafter which the solvent was distilled off

출처 및 근거

ORD 기록
ord-6159bcdeaad54808bdf0620c4b2581a8
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06242471B1

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