Trichloroacetonitrile → HCID 131732526, compound

HRID 869119Notes

Reaction equation

HRID 869119 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])=[O:5])#[N:2].C([O-])(=O)C.[Na+].[Cl:20][C:21]([Cl:25])([Cl:24])[C:22]#[N:23]>C(O)C>[NH2:23][C:22]([C:21]([Cl:25])([Cl:24])[Cl:20])=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 517045Sodium AcetateHCID 904089092-cyano-N-(4-methoxypyridin-3-yl)acetamide

Product 1

HCID 131732526HCID 131732526, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Cyano-N-(4-methoxy-3-pyridyl)acetamide 8 (26.4 g, 138.1 mmol) was slurried in ethanol (300 mL). Sodium acetate (23.56 g, 287.2 mmol) was added followed by trichloroacetonitrile (23.92 g, 16.85 mL, 165.7 mmol). The mixture was stirred at room temperature overnight. The suspension was filtered and the solids washed with ethanol. The solids (46.5 g) were slurried for 90 minutes in 10% aqueous ethanol, filtered and dried to afford 3-amino-4,4,4-trichloro-2-cyano-N-(4-methoxy-3-pyridyl)but-2-enamide (37.2 g, 80%). LC-MS (M+H)+ 336.9; 1H NMR (500 MHz, DMSO-d6) δ 8.44 (d, 1H), 7.43-7.47 (m, 1H), 6.35-6.39 (m, 1H), 4.04 (s, 3H).

Workup

  1. filtrationThe suspension was filtered
  2. washthe solids washed with ethanol
  3. waitThe solids (46.5 g) were slurried for 90 minutes in 10% aqueous ethanol
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-efdc255694c141a0bb33624a38d48744
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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