Hydrochloric Acid → 3-amino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide

HRID 1943091Notes

Reaction equation

S(=[N:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=1[CH2:27][CH3:28])=[O:8])=O.Cl>ClCCl.O1CCCC1>[NH2:3][C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[C:7]([NH:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:23])([F:24])[F:25])[C:18]([F:19])([F:20])[F:21])=[CH:12][C:11]=1[CH2:27][CH3:28])=[O:8]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 3-sulfinylamino-N-[2-ethyl-6-methyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.111 g, 0.237 mmol) (for example, Example 2.1) in dichloromethane (2 ml) and tetrahydrofuran (2 ml) was treated with aqueous hydrochloric acid (2N) (1 ml) and stirred at 25° C. for 30 minutes. The organic solvents were removed from the reaction mixture under reduced pressure. The residue was neutralized with aqueous sodium hydrogen carbonate (saturated) and was extracted with dichloromethane. The organic phase was dried over sodium sulfate and evaporated to yield the desired compound. 1H-NMR (CDCl3, 400 MHz): 7.44 (s, 1H), 7.38 (s, 2H), 7.30-7.20 (m, 3H), 6.89 (d, 1H), 3.85 (bs, 2H), 2.69 (q, 2H), 2.32 (s, 3H), 1.22 (t, 3H) ppm.

Workup

customThe organic solvents were removed from the reaction mixture under reduced pressure
extractionwas extracted with dichloromethane
dry with materialThe organic phase was dried over sodium sulfate
customevaporated

Sources & evidence

ORD record: ord-5b869890caab407eb2019df508d11e34
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389767B2

Reaction notes

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