Propyl mercaptan → 3-(2-Propylthio-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

HRID 2266028Notes

Reaction equation

Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.[CH2:17]([SH:20])[CH2:18][CH3:19].[H-].[Na+]>>[CH2:17]([S:20][C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1)[CH2:18][CH3:19]

Participants

Reactant 3

HCID 7848Propyl mercaptan

HCID 24758Sodium hydride

HCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687820003-(2-Propylthio-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 40.9%

Procedure

3-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (243 mg, 0.966 mmol) was reacted with propanthiol (229 mg, 3.01 mmol) and sodium hydride (145 mg, 3.62 mmol) to afford title compound (115 mg) after purification by column chromatography (Hex EtOAc=2/3).

Sources & evidence

ORD record: ord-e2fdece70e554f36b9f05f95e76a3e8d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858621B2

Reaction notes

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