Triethylamine → HCID 73986581, compound

HRID 279103Notes

Reaction equation

[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([N:13]([C:15](SC)=[C:16]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:17]#[N:18])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:33][CH:34]([NH2:39])[C:35]([CH3:38])([CH3:37])[CH3:36].C(N(CC)CC)C>C(#N)C>[F:32][C:2]([F:1])([F:31])[C:3]1[CH:4]=[C:5]([N:13]([C:15]([NH:39][CH:34]([CH3:33])[C:35]([CH3:38])([CH3:37])[CH3:36])=[C:16]([S:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:17]#[N:18])[CH3:14])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-[N-(3,5-Bis(trifluoromethyl)phenyl)-N-methylamino]-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.300 g, 0.58 mmol) in dry acetonitrile (2 ml) was added 1,2,2-trimethylpropylamine (0.12 g) and dry triethylamine (89 μl). The mixture was stirred for 68 h at 80° C. under nitrogen. The reaction mixture was concentrated. Purification by flash chromatography using ethyl acetate/heptane 1:4 and 1:3 as eluent gave a syrup (142 mg) which was crystallised in ethanol/water to give 110 mg (33%) of the title compound. Mp 151.5-154° C. 1H NMR (300 MHz, CDCl3): δ=0.9 (s, 9H), 1.10 (d, 3H), 3.11 (m, 1H), 3.30 (s, 3H), 7.10 (s, 2H), 7.46 (s, 1H), 7.55 (d, 2H), 7.85 (d, 2H), 8.1 (br d, 1H); MA calc for C24H24ClF6N3O2S: C, 50.75%; H, 4.26%; N, 7.40%; Cl, 6.24%. Found: C, 50.79%; H, 4.28%; N, 7.24%; Cl, 6.19%.

Workup

concentrationThe reaction mixture was concentrated
customPurification by flash chromatography

Sources & evidence

ORD record: ord-32c533b5f3434e02bbd0a76288657a17
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362205B1

Reaction notes

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