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Thioacetamide → Ethyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-6-carboxylate

HRID 2040335
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HRID 2040335 반응식
Br[CH:2]1[C:7](=O)[CH2:6][CH2:5][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3]1.[C:14](=[S:17])([NH2:16])[CH3:15]>CN(C)C=O>[CH3:15][C:14]1[S:17][C:2]2[CH2:3][CH:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:6][C:7]=2[N:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 2723949ThioacetamideHCID 12917737Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

생성물 1

HCID 12917745Ethyl 2-methyl-4,5,6,7-tetrahydrobenzo[d]thiazole-6-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of EXAMPLE 387A (4.4 g) and ethanethioamide (1.33 g) in N,N-dimethylformamide (50 mL) was heated at 140° C. for 20 hours. After it cooled to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate three times. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica to give the title compound.

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후처리

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica

출처 및 근거

ORD 기록
ord-349f54bfa70f422d8f79814062b9a8bd
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08580794B2

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