3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile → 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-isopropylamino-2-propenenitrile

HRID 279090Notes

Reaction equation

HRID 279090 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14](SC)=[C:15]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>C(N)(C)C>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:13][CH:5]([CH3:6])[CH3:4])=[C:15]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

3

Reactant 1

HCID 865837313-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 865837323-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-isopropylamino-2-propenenitrileYield 124.1%

Reagents, catalysts & solvents 1

HCID 6363IsopropylamineSolvent

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.400 g, 0.8 mmol) was stirred in isopropylamine (2 ml) at 80° C. in a sealed flask for 20 h. Work up as described in Example 1, 2) gave 254 mg (62%) of the title compound as white crystals. Mp 197-198.5° C. 1H NMR (300 MHz, CDCl3): δ=1.5 (d, 6H), 3.37 (m, 1H), 7.42 (s, 2H), 7.48 (d, 2H), 7.67 (s, 1H), 7.79 (d, 2H); MA calc for C20H16ClF6N3O2S: C, 46.93%; H, 3.15%; N, 8.21%. Found: C, 47.16%; H, 3.14%; N, 8.10%.

Sources & evidence

ORD record
ord-5f81b62c6bba4a4abc9124b479aee18c
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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