Dimethylformamide → HCID 86617329, compound

HRID 1960210Notes

Reaction equation

HRID 1960210 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7](Cl)(=[O:9])[CH3:8].CN(C=O)C.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]([O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:25]=[CH:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:19][CH:18]=1>COC(C)(C)C>[C:7]([O:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]([O:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:25]=[CH:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:19][CH:18]=1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 86617327HCID 86617327, compound

Product 1

HCID 86617329HCID 86617329, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Potassium carbonate (0.075 g) and acetyl chloride (0.035 ml) were added to DMF (3 ml) solution of phenyl N-(4-hydroxyphenyl)-3-(phenoxy)acrylimidate (0.15 g) at room temperature and stirred for two hours at the same temperature and for three hours at 50° C. t-Butyl methyl ether (80 ml) was added to the reaction solution, and it was successively washed with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain phenyl N-(4-acetoxyphenyl)-3-(phenoxy)acrylimidate (0.11 g) as colorless oil.

Workup

  1. additionwas added to the reaction solution, and it
  2. washwas successively washed with water and aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-340a07c031294d55b82c603a0d9b5bae
Source dataset
uspto-grants-2013_04
Patent number
US08410316B2

Reaction notes

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