2-Butanamine, 3,3-dimethyl- → 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile

HRID 279100Notes

Reaction equation

HRID 279100 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.[CH3:26][CH:27]([NH2:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>>[F:1][C:2]([F:24])([F:25])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:32][CH:27]([CH3:26])[C:28]([CH3:31])([CH3:30])[CH3:29])=[C:15]([S:18]([CH3:21])(=[O:20])=[O:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 739865843-(3,5-Bis(trifluoromethyl)phenylamino)-2-methanesulfonyl-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 739865823-(3,5-Bis(trifluoromethyl)phenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrileYield 57%

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methylsulfonyl-3-methylsulfanyl-2-propenenitrile (0.225 g, 0.56 mmol) was stirred in 1,2,2-trimethylpropylamine (1 ml) for 22 h at 100° C. under nitrogen in a sealed flask. The reaction mixture was concentrated and the residue dissolved in DCM, washed twice with 1N aqueous HCl and once with water. The organic phase was dried (sodium sulfate) and concentrated. The residue was crystallised from ethyl acetate/heptane 1:4 to give 146 mg (57%) of the title compound. Mp 184.5-188.5° C. 1H NMR (200 MHz, CDCl3): δ=0.9 (s, 9H), 1.03 (d, 3H), 3.0 (m, 1H), 7.52 (s, 2H), 7.68 (s, 1H); EI SP/MS: 457 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in DCM
  3. washwashed twice with 1N aqueous HCl and once with water
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. concentrationconcentrated
  6. customThe residue was crystallised from ethyl acetate/heptane 1:4

Sources & evidence

ORD record
ord-069ee5e01c534585bf66610f366065e2
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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