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

HRID 130488
Notes
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Reaction equation

HRID 130488 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 23670855Potassium ethanethioateHCID 58599386HCID 58599386, compoundHCID 178418634HCID 178418634, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

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)

Workup

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

Sources & evidence

ORD record
ord-fa1d6c30f4e54bf897e37593737a8754
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07381749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes