Toluene → 0-cyclopropylmethyl N-phenylacetyl-(2,6-dichlorophenyl)-acetamidoxime

HRID 2212058Notes

Reaction equation

HRID 2212058 reaction equation
C1(C[C:5]2([Cl:17])[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]2[CH2:12][C:13](=[N:15][OH:16])[NH2:14])CC1.[C:18]1([CH2:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+].[C:33]1([CH3:39])[CH:38]=[CH:37]C=CC=1>>[CH:38]1([CH2:37][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:24][C:25]([NH:14][C:13](=[N:15][OH:16])[CH2:12][C:6]2[C:7]([Cl:11])=[CH:8][CH:9]=[CH:10][C:5]=2[Cl:17])=[O:26])[CH2:33][CH2:39]1

Participants

5

Reactant 4

HCID 1140TolueneHCID 7679Phenylacetyl chlorideHCID 516892Sodium BicarbonateHCID 1317259160-Cyclopropylmethyl (2,6-dichlorophenyl)acetamidoxime

Product 1

HCID 1372420200-cyclopropylmethyl N-phenylacetyl-(2,6-dichlorophenyl)-acetamidoxime

Conditions

Temperature
100 °C

Procedure

5.0 g (18 mmol) of 0-cyclopropylmethyl (2,6-dichlorophenyl)acetamidoxime in 40 ml of toluene were heated to 85° C and admixed with 3.9 g (25 mmol) of phenylacetyl chloride. The mixture was heated at 100° C. for 5 h, cooled, poured into aqueous sodium hydrogen carbonate solution (pH 7) and extracted three times with toluene. The combined extracts were washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product (5.6 g) was purified by silica gel chromatography using cyclohexane/ethyl acetate. M.p. 134–135° C.

Workup

  1. temperaturecooled
  2. extractionextracted three times with toluene
  3. washThe combined extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product (5.6 g) was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e65edce304774709b9289615e9c9e9ef
Source dataset
uspto-grants-2006_09
Patent number
US07101900B2

Reaction notes

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