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Toluene → HCID 59135737, compound

HRID 1960584
Notes
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Reaction equation

HRID 1960584 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19](=[S:21])[NH2:20])=[CH:15]2)(=[O:8])=[O:7].[C:22]([O:27][CH2:28][CH3:29])(=[O:26])[C:23]#[C:24][CH3:25].C(P(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:21][CH:24]([CH2:23][C:22]([O:27][CH2:28][CH3:29])=[O:26])[CH2:25][N:20]=1)=[CH:15]2)(=[O:7])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1140TolueneHCID 13831TributylphosphineHCID 78043Ethyl 2-butynoate2×HCID 57901763HCID 57901763, compound

Product 1

HCID 59135737HCID 59135737, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
60 °C

Procedure

A solution of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide (4.3 g), ethyl but-2-ynoate (3.2 mL) and tributylphosphine (3.2 mL) in tetrahydrofuran (40 mL)-toluene (40 mL) was stirred at room temperature for 2 days ethyl but-2-ynoate (1.6 mL) was added to the reaction solution again, and the mixture was stirred at 60° C. for 2 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:8-4:6) to give the title compound (1.6 g, yield: 28%) as a pale-brown oil.

Workup

  1. additionwas added to the reaction solution again
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c50ad7ea420643d28a369b57140ec016
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410087B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes