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

HRID 1943089Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH2:20])[CH3:2].[S:21](=[N:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28])=[O:22]>[2H]C(Cl)(Cl)Cl>[S:21](=[N:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH:20][C:4]1[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17])=[CH:8][C:3]=1[CH2:1][CH3:2])=[O:28])=[O:22]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (0.100 g, 0.33 mmol) (prepared according to EP 1,006,102) in deuterochloroform (1.0 ml) was added under stirring at 25° C., a solution of 3-sulfinylamino-benzoyl chloride (0.033 g, 0.165 mmol) (Example 1.1) in dry deuterochloroform (1.0 ml). After stirring for 8 hours at 40° C., a sample of the reaction mixture was submitted to 1H-NMR spectroscopy. The desired compound was detected in the reaction mixture, based on its characteristic signals (see 1H-NMR spectral data as described in Example 2.2), together with unreacted starting materials. Integration of the signals showed a conversion of 85%. An aliquot of the reaction mixture was diluted in dry acetonitrile and was submitted to mass spectrometry via direct injection (same conditions as described in Example 2.1). Calculated exact mass: 468; [M-H]− observed: 467.06.

Workup

stirringAfter stirring for 8 hours at 40° C.

Sources & evidence

ORD record: ord-69b63c98d95c4da693c05f528fefd2c9
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389767B2

Reaction notes

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