3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenylsulfonyl)-3-methylsulfanyl-2-propenenitrile → HCID 73986583, compound

HRID 279092Notes

Reaction equation

HRID 279092 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)CC>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:13][CH2:5][CH2:4][CH3:3])=[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:12])[F:10])[CH:8]=1

Participants

3

Reactant 1

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

Product 1

HCID 73986583HCID 73986583, compoundYield 129.9%

Reagents, catalysts & solvents 1

HCID 7852PropylamineSolvent

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chlorophenyisulfonyl)-3-methylsulfanyl-2-propenenitrile (0.400 g, 0.8 mmol) was stirred in n-propylamine (1.0 ml) at 75° C. in a sealed flask for 19 h. Work up as described in Example 1, 2) gave 266 mg (65%) of the title compound as white crystals. Mp 196.5-198.5° C. 1H NMR (300 MHz, CDCl3): δ=0.9 (t, 3H), 1.55 (p, 2H), 2.88 (q, 2H), 7.40 (s, 2H), 7.48 (d, 2H), 7.68 (s, 1H), 7.81 (d, 2H); MA calc for C20H16ClF6N3O2S: C, 46.93%; H, 3.15%; N, 8.21%. Found: C, 46.82%; H, 3.19%; N, 8.10%.

Sources & evidence

ORD record
ord-9f711ce290c04081a3feeec78d559b2f
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

Loading…