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

HRID 1943090Notes

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].C(=O)([O-])[O-].[K+].[K+].[S:27](=[N:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34])=[O:28]>[2H]C(Cl)(Cl)Cl>[S:27](=[N:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([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:34])=[O:28]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenylamine (0.082 g, 0.27 mmol) (prepared according to EP 1,006,102) and finely ground potassium carbonate (0.112 g, 0.81 mmol) in deuterochloroform (1.0 ml) under stirring at 25° C., was added 3-sulfinylamino-benzoyl chloride (0.055 g, 0.27 mmol) (Example 1.1) dissolved in dry deuterochloroform (1.0 ml). The reaction mixture was stirred at 40° C. for 16 hours. A sample of the supernatant 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. 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: 467.00.

Workup

stirringThe reaction mixture was stirred at 40° C. for 16 hours

Sources & evidence

ORD record: ord-d2b661495f5e4808a418543006c51a52
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389767B2

Reaction notes

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