Dimethylformamide → HCID 57667990, compound

HRID 2191631Notes

Reaction equation

HRID 2191631 reaction equation
[CH3:1]N(C)C=O.[NH2:6][C:7]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>C(OCC)(=O)C>[NH2:6][C:7]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:1])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 57667856HCID 57667856, compound

Product 1

HCID 57667990HCID 57667990, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N,N-dimethylformamide 5.0 mL solution of 2-amino-4-phenoxybenzoic acid 0.40 g were added potassium carbonate 0.29 g and dimethyl sulfate 0.20 mL, and it was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture, it was dried over anhydrous magnesium sulfate after sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=10:1] to give methyl 2-amino-4-phenoxybenzoate 0.33 g of colorless oil.

Workup

  1. dry with materialwas dried over anhydrous magnesium sulfate
  2. washafter sequential washing with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fb755a90d4e540098f138011462c30fd
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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