Water → HCID 86737669, compound

HRID 443348Notes

Reaction equation

HRID 443348 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-d8cca10292bb4546bec627a3e0da3fd2
Source dataset
uspto-grants-1981_04
Patent number
US04260410

Reaction notes

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