Dimethyl Sulfate → HCID 54013338, compound

HRID 261511Notes

Reaction equation

HRID 261511 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:15])[C:12]([OH:14])=[O:13].[C:21](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:15])[C:12]([O:14][CH3:21])=[O:13]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 15646809HCID 15646809, compound

Product 1

HCID 54013338HCID 54013338, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 12.4 g of 2-(2,6-dichloroanilino)-phenylglyoxylic acid in 80 ml of anhydrous acetone were added 6.05 g of anhydrous potassium carbonate and then 7.5 ml of dimethyl sulfate at room temperature, and the mixture was stirred for 1 hour. The reaction mixture was filtered and washed with anhydrous acetone. The filtrate was concentrated under 10 mmHg without heating. The residue was recrystallized from ethanol to give 12.3 g of methyl 2-(2,6-dichloroanilino)phenylglyoxylate as yellow prisms. m.p. 124.5-125.5° C. Yield: 95% of theoretical amount

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with anhydrous acetone
  3. concentrationThe filtrate was concentrated under 10 mmHg
  4. temperaturewithout heating
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8d34baaefb1348f6ad076ed505a55ee1
Source dataset
uspto-grants-1979_08
Patent number
US04166128

Reaction notes

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