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2-Propanethiol → Methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate

HRID 2226857
Notes
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Reaction equation

HRID 2226857 reaction equation
[CH3:1][CH:2]([SH:4])[CH3:3].Cl[C:6]1[C:7]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:8]=2[S:9][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1)=[O:12].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C=O)C.C(OCC)(=O)C>[CH3:29][O:28][C:26]1[CH:25]=[CH:24][C:8]2[S:9][C:10]([C:11]([NH:13][C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=3)=[O:12])=[C:6]([S:4][CH:2]([CH3:3])[CH3:1])[C:7]=2[CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 19225607Methyl 4-[[[3-chloro-5-methoxybenzo[b]thien-2yl]carbonyl]amino]benzoateHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18963770Methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoateYield 72%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

2-Propanethiol (32 μL, 0.35 mmol) is added to a solution of methyl 4-[[[3-chloro-5-methoxybenzo[b]thien-2yl]carbonyl]amino]benzoate (100 mg, 0.27 mmol) in 1 mL of DMF. Diazabicycloundecene (DBU) (52 μL, 0.35 mmol) is added and the mixture is stirred at room temperature for 5 hours. The reaction mixture is diluted with ethyl acetate and washed with 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives methyl 4-[[[5-methoxy-3-[(1-methylethyl)thio]benzo[b]thien-2yl]carbonyl]amino]benzoate in 72% yield; mp=157.5°-158.5° C.

Workup

  1. washwashed with 1N HCl, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationFiltration
  4. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-70154838cbbe48dc97a89109d2f02ab7
Source dataset
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05350748

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes