2-Aminothiophenol → HCID 19969451, compound

HRID 974799Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].F[C:12]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].CCCCCC.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:12]1[CH:19]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Aminothiophenol (8.17 g, 65 mmol) was added to a mixture of sodium hydride (2.35 g of 80% dispersion, 1.2 eq) in dimethylformamide (DMF, 100 ml) at 0° C. under a nitrogen atmosphere. After stirring for 30 mins 2-fluoro-4-trifluoromethylbenzonitrile (11.68 g, 0.95 eq) was added and the reaction mixture stirred at 0° C. for 1 hr then kept at 10° C. overnight. The solvent was evaporated in vaccuo and the residue taken up in ether (100 ml) and washed with sodium bicarbonate solution (1M, 100 ml). The organic layer was separated and dried (sodium sulphate, Na2SO4), and evaporated to give a yellow solid. The title compound (12.5 g, m.p. 102°-104° C., Rf 0.67, hexane/EtOAc 2:1) was obtained in pure form by chromatography on silica eluting first with hexane/ethyl acetate (6:1) then (4:1).

Workup

additionwas added
waitthen kept at 10° C. overnight
customThe solvent was evaporated in vaccuo
washwashed with sodium bicarbonate solution (1M, 100 ml)
customThe organic layer was separated
dry with materialdried (sodium sulphate, Na2SO4)
customevaporated
customto give a yellow solid

Sources & evidence

ORD record: ord-774e44a8ea7d4d48a9f979dc20887268
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05607929

Reaction notes

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