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

HRID 279129Notes

Reaction equation

HRID 279129 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([NH:13][C:14](SC)=[C:15]([S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH2:28][CH:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH3:30]>>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:28][CH:29]([CH3:30])[C:31]([CH3:34])([CH3:33])[CH3:32])=[C:15]([S:18]([CH:21]([CH3:22])[CH3:23])(=[O:19])=[O:20])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 865837393-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile

Product 1

HCID 865841113-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrileYield 80%

Procedure

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-methylsulfanyl-2-propenenitrile (0.500 g, 0.6 mmol) was stirred in 2-amino-3,3-dimethylbutane (1 ml) for 48 h at 100° C. under nitrogen in a sealed flask. The reaction mixture was concentrated and the residue dissolved in dichloromethane, washed twice with 1N aqueous HCl, once with brine, and once with water. The organic phase was dried (sodium sulphate) and evaporated to afford 450 mg (80%) of the title compound as pale yellow crystals. Mp 177-180° C. 1H NMR (200 MHz, CDCl3): δ=0.89 (s, 9H), 1.04 (d, 3H), 1.40 (d, 6H), 2.97 (m, 1H), 3.27 (m, 1H), 7.50 (s, 2H), 7.67 (s, 1H), 9.16 (brs, 1H);

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed twice with 1N aqueous HCl, once with brine
  4. dry with materialThe organic phase was dried (sodium sulphate)
  5. customevaporated

Sources & evidence

ORD record
ord-5269dc0c7ae0403a8eabef79cc9b2ea2
Source dataset
uspto-grants-2002_03
Patent number
US06362205B1

Reaction notes

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