Water → HCID 86737669, compound

HRID 2286046Notes

Reaction equation

HRID 2286046 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([CH:8]([NH:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:9])[CH3:7])[CH:2]=[CH2:3].N1C=CC=CC=1.[Cl:25][CH2:26][C:27](Cl)=[O:28].O>C(OCC)(=O)C>[CH2:1]([O:4][N:5]=[C:6]([CH:8]([N:10]([C:11]1[C:12]([CH3:18])=[CH:13][CH:14]=[CH:15][C:16]=1[CH3:17])[C:27](=[O:28])[CH2:26][Cl:25])[CH3:9])[CH3:7])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 86737670HCID 86737670, compound

Product 1

HCID 86737669HCID 86737669, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(2,6-dimethylphenylamino)-2-butanone O-allyl oxime (4.5 g) in 75 ml ethyl acetate and 1.6 g pyridine was added dropwise 2.3 g chloroacetyl chloride. The mixture was stirred for 15 minutes, and poured into 1 liter of water. The organic phase was collected, diluted with 100 ml ether, washed with water, dried (MgSO4), treated with silica gel and stripped of solvent to yield 4.9 g yellow oil. The oil was chromatographed on silica gel (125 g) with elution by 3:1 CH2Cl2 :hexane followed by 5% acetone:CH2Cl2, to yield 2.5 g of the title product. This compound is tabulated as Compound No. 20 in Table I.

Workup

  1. customThe organic phase was collected
  2. additiondiluted with 100 ml ether
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. additiontreated with silica gel

Sources & evidence

ORD record
ord-cf0dd447cac944d38754c260d0da0c6c
Source dataset
uspto-grants-1982_04
Patent number
US04326077

Reaction notes

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