2-Butanamine, 3,3-dimethyl- → 3-(4-Chlorophenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile

HRID 840232Notes

Reaction equation

HRID 840232 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](SC)=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[C:11]#[N:12])=[CH:4][CH:3]=1.[CH3:19][CH:20]([NH2:25])[C:21]([CH3:24])([CH3:23])[CH3:22]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:25][CH:20]([CH3:19])[C:21]([CH3:24])([CH3:23])[CH3:22])=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[C:11]#[N:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 701491873-(4-Chlorophenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile

Product 1

HCID 701491893-(4-Chlorophenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrileYield 85%

Procedure

3-(4-Chlorophenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile (0.242 g, 0.8 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 0.240 g (85%) of the title compound. Mp 160.5-161.5° C. 1H NMR (200 MHz, CDCl3): δ=0.87 (s, 9H), 0.97 (d, 3H), 3.1 (m, 4H), 7.07 (d, 1H), 7.49 (d, 2H); Analysis: calc. for C16H22ClN3O2S: C, 54.00%; H, 6.23%; N, 11.81%; Found: C, 54.26%; H, 6.33%; N, 11.76%.

Sources & evidence

ORD record
ord-dcca92546bd04720a4c14d417202e2e6
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Reaction notes

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