Lawesson's reagent → 2,3-Difluoro-4-(trifluoromethyl)benzene-1-carbothioamide

HRID 1767969Notes

Reaction equation

[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:25]2)=CC=1>O1CCCC1>[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[S:25]

Participants

Conditions

Temperature: 130 °C

Procedure

A suspension of 2,3-difluoro-4-trifluoromethyl-benzamide (1 g, 4.4 mmol) and 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent; 900 mg, 2.2 mmol) in tetrahydrofuran (2 ml) was stirred under microwave irradiation at 130° C. for 15 min. The solvent was removed under reduced pressure to give an orange oil which was purified by column chromatography (silica gel, heptane/AcOEt) to yield 1.0 g (4.1 mmol, 93%) of the title compound as yellow crystals.

Workup

customThe solvent was removed under reduced pressure
customto give an orange oil which
customwas purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record: ord-dca064b78e2446449994d664c1116ba0
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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