2-Butanamine, 3,3-dimethyl- → HCID 70149492, compound

HRID 279119Notes

Reaction equation

HRID 279119 reaction equation
[CH3:1][O:2][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.[CH3:24][CH:25]([NH2:30])[C:26]([CH3:29])([CH3:28])[CH3:27]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:30][CH:25]([CH3:24])[C:26]([CH3:29])([CH3:28])[CH3:27])=[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

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 70150566HCID 70150566, compound

Product 1

HCID 70149492HCID 70149492, compoundYield 40%

Procedure

3-(3-Methoxy-5-trifluoromethyl-phenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile (0.22 g, 0.6 mmol) was stirred in 1,2,2-trimethylpropylamine (1 ml) for 17 h at 75° C. under nitrogen. Work-up as described in EXAMPLE 17, 2) without chromatography gave 100 mg (40%) of the title compound. Mp 110-113° C. 1H NMR (200 MHz, CDCl3): δ=0.87 (s, 9H), 1.01 (d, 3H), 3.08 (m, 1H), 3.10 (s, 3H), 3.87 (s, 3H), 6.81 (br s, 1H), 6.95 (br s, 1H), 6.97 (br s, 1H); Analysis: calc. for C18H24N3O3S: C, 51.54%; H, 5.77%; N, 10.02%; Found: C, 51.77%; H, 6.05%; N, 9.80%.

Sources & evidence

ORD record
ord-92977ee90aad43e4a1a4999197e83873
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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