Phenyl thioxochloroformate → HCID 118250840, compound

HRID 1488211Notes

Reaction equation

[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]([OH:18])[C:14]([F:17])([F:16])[F:15])[C:10](C)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:21](=[S:29])[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:21](=[S:29])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:18][CH:13]([C:11]1[CH:10]=[N:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=1)[C:14]([F:15])([F:16])[F:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(1-benzyl-3-methyl-1H-pyrazol-4-yl)-2,2,2-trifluoroethanol (compound 314.3, 1.15 g, 4.26 mmol) in toluene (15 mL) were added 4-dimethylaminopyridine (1.47 g, 12.0 mmol) and phenyl chloromethanethioate (1.04 g, 6.02 mmol). The reaction mixture was stirred for 1 h at 60° C. under nitrogen, then concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/15) as the eluent to yield 1.34 g (77%) of the title compound as a light yellow oil.

Workup

concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/15) as the eluent

Sources & evidence

ORD record: ord-7c1d977e6ae542e68d9d90800a10803b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428502B2

Reaction notes

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