Acetyl chloride → HCID 15292069, compound

HRID 2396749Notes

Reaction equation

HRID 2396749 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([N:13]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]=1[NH2:28])[CH2:2][CH2:3][CH3:4].[C:29](Cl)(=O)[CH3:30].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:6]2[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([N:13]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:7]=2[N:28]=[C:29]1[CH3:30])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24813Phosphorus oxychlorideHCID 70282540HCID 70282540, compound

Product 1

HCID 15292069HCID 15292069, compoundYield 26.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N4 -n-Butyl-6-methyl-N2,N2 -bis(phenylmethyl)pyridine-2,3,4-triamine (0.65 g, 1.7 mmole) was combined with toluene (10 mL) and acetyl chloride (0.12 mL, 1.7 mmole) and stirred at ambient temperature for 15 minutes. Phosphorous oxychloride (0.31 mL) was added and the reaction mixture was heated at reflux overnight. The reaction mixture was evaporated. The residue was purified by silica gel column chromatography eluting with hexane:ethyl acetate (70:30) to provide 0.18 g of the desired product.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customThe reaction mixture was evaporated
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with hexane:ethyl acetate (70:30)

Sources & evidence

ORD record
ord-336fe73ecca8437a94a69d935f182d12
Source dataset
uspto-grants-1996_02
Patent number
US05494916

Reaction notes

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