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Dichloromethane → Thioacetic acid S-[2-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-2-oxo-ethyl]ester

HRID 130488
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HRID 130488 반응식
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19](=[O:22])[CH2:20]Br)=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([O-:26])(=[S:25])[CH3:24].[K+].ClCCl.C(O)(=S)C>CO>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19](=[O:22])[CH2:20][S:25][C:23](=[O:26])[CH3:24])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 23670855Potassium ethanethioateHCID 58599386HCID 58599386, 화합물HCID 178418634HCID 178418634, 화합물

생성물 1

HCID 11552545Thioacetic acid S-[2-(1-benzenesulfonyl-2,3-dihydro-1H-indol-5-yl)-2-oxo-ethyl]ester

시약·촉매·용매 1

HCID 887Methanol
용매

실험 절차

The mono-brominated sulfonamide from step 2 (0.194 g, 0.509 mmol) was was dissolved in methanol (2 ml) before potassium thioacetate (0.0639 g, 0.560 mmol) was added as a solid. LC-MS of the resulting yellow solution shows the reaction is complete in minutes. Evaporation of the volatiles leaves a tan residue which was taken up into dichloromethane (4 ml), during which the disulfide of the thioacetic acid was deposited and filtered. The desired thioester could then be recrystallized from dichloromethane/hexanes (0.080 g, 0.214 mmol, 42%). LC-MS (ES+): 376 [MH]+ m/e. 1H-NMR (DMSO): 7.87 (d, 3H), 7.78 (s, 1H), 7.7 (m, 1H), 7.57 (m, 3H), 4.41 (s, 2H), 3.99 (t, 2H), 3.06 (t, 2H), 2.34 (s, 3H)

후처리

  1. additionwas added as a solid
  2. waitis complete in minutes
  3. customEvaporation of the volatiles
  4. customleaves a tan residue which
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-fa1d6c30f4e54bf897e37593737a8754
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07381749B2

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