Cyclopentylamine → 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-cyclopentylamino2-propenenitrile

HRID 279089Notes

Reaction equation

HRID 279089 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.[CH:32]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33]1>>[F:31][C:2]([F:30])([F:1])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:37][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[C:15]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)(=[O:19])=[O:20])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 865837313-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 739865863-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-cyclopentylamino2-propenenitrileYield 71%

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.400 g, 0.8 mmol) was stirred in cyclopentylamine (2 ml) at 80° C. for 2 h and at room temperature for 16 h under nitrogen. Work up as descriped in Example 1, 2) gave 305 mg (71%) of the title compound as pale yellow crystals. Mp 199-200° C. 1H NMR (300 MHz, CDCl3): δ=1.4-1.65 (m, 4H), 1.65-1.85 (m, 4H), 3.56 (sextet, 1H), 7.42 (s, 2H), 7.49 (d, 2H), 7.67 (s, 1 H), 7.78 (d, 2H); MA calc for C22H18ClF6N3O2S: C, 49.12%; H, 3.37%; N, 7.18%. Found: C, 48.93%; H, 3.31%; N, 7.58%.

Sources & evidence

ORD record
ord-8277ddd4845e4a72ad8b6d719fcc29eb
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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