Acetic Anhydride → Ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

HRID 1108339노트

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HRID 1108339 반응식
[N:1]([CH:4]1[CH2:19][CH2:18][C:7]2=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:9][C:10]([S:11][CH3:12])=[C:6]2[C:5]1=[O:20])=[N+]=[N-].[C:21](OC(=O)C)(=[O:23])[CH3:22]>[C].[Pd].C(O)(=O)C>[C:21]([NH:1][CH:4]1[CH2:19][CH2:18][C:7]2=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:9][C:10]([S:11][CH3:12])=[C:6]2[C:5]1=[O:20])(=[O:23])[CH3:22]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 18388306Ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo(c]thiophene-1-carboxylate

생성물 1

HCID 12043499Ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate수율 73.8%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 176Acetic Acid용매

실험 절차

A mixture of ethyl 5-azido-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (3.62 g), palladium-carbon (5%, 50% wet, 4.0 g), acetic acid (70 ml) and acetic anhydride (35 ml) was subjected to a catalytic reduction reaction at room temperature under 1 atm. The insoluble substances were filtered off; the filtrate was concentrated under reduced pressure; the residue was dissolved in ethyl acetate-tetrahydrofuran (3:1, v/v). This solution was washed with water, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off to yield ethyl 5-acetylamino-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.81 g, 73.8%), which was then recrystallized from chloroform-ethanol. Colorless needles. Melting point 215-216° C.

후처리

  1. customwas subjected to a catalytic reduction reaction at room temperature under 1 atm
  2. filtrationThe insoluble substances were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate-tetrahydrofuran (3:1
  5. washThis solution was washed with water
  6. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  7. distillationafter which the solvent was distilled off

출처 및 근거

ORD 기록
ord-53ada937ba994cfb96bbbe56d9ecb513
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066658

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