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

HRID 1943088Notes

Reaction equation

[S:1](=[N:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])=[O:2].[CH2:13]([C:15]1[CH:20]=[C:19]([C:21]([F:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:18]=[C:17]([CH3:31])[C:16]=1[NH2:32])[CH3:14]>[2H]C(Cl)(Cl)Cl>[S:1](=[N:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:32][C:16]1[C:17]([CH3:31])=[CH:18][C:19]([C:21]([F:30])([C:22]([F:23])([F:24])[F:25])[C:26]([F:27])([F:28])[F:29])=[CH:20][C:15]=1[CH2:13][CH3:14])=[O:8])=[O:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-sulfinylamino-benzoyl chloride (0.033 g, 0.165 mmol) (Example 1.1) in dry deuterochloroform (0.5 ml) was added under stirring at 25° C., a solution of 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (0.050 g, 0.165 mmol) (prepared according to EP 1,006,102) in deuterochloroform (0.5 ml). After stirring for 60 hours at 25° C., a sample of the reaction mixture was submitted to 1H-NMR spectroscopy. The desired compound was detected in the reaction mixture together with unreacted starting materials. Integration of the signals showed a conversion of 40%. 1H-NMR (CDCl3, 400 MHz): 8.35 (s, 1H), 8.07 (d, 1H), 7.95 (d, 1H) 7.58 (t, 1H), 7.49 (s, 1H), 7.37 (s, 2H), 2.70 (q, 2H), 2.31 (s, 3H), 1.22 (t, 3H) ppm.

Workup

stirringAfter stirring for 60 hours at 25° C.

Sources & evidence

ORD record: ord-c0e6970bcda2492e9e93c95d1a8a67cc
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389767B2

Reaction notes

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