3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile → 3-(3,5-Bis(trifluoromethyl)phenylamino)-3-isopropylamino-2-methylsulfonyl-propenenitrile
Reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](SC)=[C:15]([S:18]([CH3:21])(=[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:12][C:9]([F:11])([F:10])[C:7]1[CH:6]=[C:5]([NH:13][C:14]([NH:13][CH:5]([CH3:6])[CH3:4])=[C:15]([S:18]([CH3:21])(=[O:19])=[O:20])[C:16]#[N:17])[CH:4]=[C:3]([C:2]([F:24])([F:25])[F:1])[CH:8]=1Participants
3
Procedure
3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile (0.323 g, 0.8 mmol) was stirred in isopropylamine (1 ml) for 17 h at 75° C. under nitrogen. Work-up as described in Example 17, 2) without chromatography gave 247 mg (74%) of the title compound. Mp 188.5-191° C. 1H NMR (200 MHz, CDCl3): δ=1.15 (d, 6H), 3.15 (s, 3H), 3.40 (m, 1H), 7.56 (s, 2H), 7.68 (s, 1H). Analysis: calc. for C15H15F6N3O2S: C, 43.38%; H, 3.64%; N, 10.12%. Found: C, 43.52%; H, 3.63%; N, 9.98%.
Sources & evidence
- ORD record
- ord-571b04eb26344cef99d9f8028786ed49
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06365609B1
Reaction notes
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