Thionyl Chloride → 3-sulfinylamino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943095Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH2:25][CH3:26])=[O:6].[S:30](Cl)(Cl)=[O:31]>C(Cl)(Cl)(Cl)Cl>[S:30](=[N:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:24])([C:20]([F:21])([F:22])[F:23])[C:16]([F:17])([F:18])[F:19])=[CH:10][C:9]=1[CH2:25][CH3:26])=[O:6])=[O:31]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 3-amino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.100 g, 0.237 mmol) (Example 4.1) in carbon tetrachloride (1 ml) was heated to 50° C. until it became a clear solution. A solution of thionyl chloride in carbon tetrachloride (1.68 M) (0.725 ml, 1.218 mmol) was added and the mixture was heated to 80° C. for one hour. The reaction mixture was evaporated under reduced pressure and the residue was triturated with cyclohexane. The suspension was filtered and the solid dried under high vacuum. The desired compound was obtained as white crystals. M.p. 100-108° C. 1H-NMR as described for Example 2.2. Mass spectrometric analysis: conditions as described for Example 2.1. Calculated exact mass: 468; [M-H]− observed: 467.06.

Workup

temperaturethe mixture was heated to 80° C. for one hour
customThe reaction mixture was evaporated under reduced pressure
customthe residue was triturated with cyclohexane
filtrationThe suspension was filtered
customthe solid dried under high vacuum

Sources & evidence

ORD record: ord-b6358a6fc40943e8a9741892df0e88b8
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389767B2

Reaction notes

Loading…