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

HRID 840238Notes

Reaction equation

HRID 840238 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 (br s, 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-23d61156ad9246e18aa829a241728c60
Source dataset
uspto-grants-2002_04
Patent number
US06365609B1

Reaction notes

Loading…