Benzyl mercaptan → HCID 57879334, compound

HRID 1673412Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16]([NH:24][C:25]1[CH:34]=[C:33](I)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:16]([NH:24][C:25]1[CH:34]=[C:33]([S:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:32]=[CH:31][C:26]=1[C:27]([O:29][CH3:30])=[O:28])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.15 mL of triethylamine and 0.068 mL of benzyl mercaptan were added to 2 mL of toluene suspension containing 0.20 g of methyl 2-(benzamido)-4-iodobenzoate, 36 mg of 1,1′-bis(diphenylphosphino)ferrocene and 24 mg of tris(dibenzylideneacetone)dipalladium(0) and stirred under nitrogen atmosphere at 80° C. for 2 hours. Insoluble were removed by filtration and the solvent was evaporated under reduced pressure. The obtained, residue was purified with silica gel column chromatography [eluent; hexane; ethyl acetate=10:1] to obtain 0.16 g of methyl 2-(benzamido)-4-(benzylthio)benzoate as white solid.

Workup

customInsoluble were removed by filtration
customthe solvent was evaporated under reduced pressure
customThe obtained, residue was purified with silica gel column chromatography [eluent; hexane; ethyl acetate=10:1]

Sources & evidence

ORD record: ord-cae0500f9f3a4bc1b30cd63b334b0dcc
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999132B2

Reaction notes

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