Dimethyl Sulfate → HCID 21835795, compound

HRID 1586551Notes

Reaction equation

HRID 1586551 reaction equation
[C:1]([CH:4]=[N:5][C:6]1[C:7](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:8](O)=[O:9])([OH:3])=[O:2].[C:16](=O)([O-])[O-].[K+].[K+].S([O:27][CH3:28])(OC)(=O)=O>CN(C)C=O>[C:1]([CH:4]=[N:5][C:6]1[C:7](=[CH:11][CH:12]=[C:13]([Cl:15])[CH:14]=1)[C:8]([O:27][CH3:28])=[O:9])([O:3][CH3:16])=[O:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 19597249HCID 19597249, compound

Product 1

HCID 21835795HCID 21835795, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17 g (66 mmol) of N-carboxymethylene-4-chloroanthranilic acid are dissolved in 175 g of N,N-dimethylformamide, and 22.5 g (162 mmol) of potassium carbonate are added. At 80° C., 56 g (444 mmol) of dimethyl sulfate are added dropwise in 3 portions over the course of 2 h, and the mixture is then stirred for 30 min. The excess dimethyl sulfate is destroyed by adding ammonia. The product is precipitated by cooling, filtered off and washed with water. 16.1 g (62.5 mmol; 95%) of methyl N-carbomethoxymethylene-4-chloroanthranilate are isolated.

Workup

  1. customThe excess dimethyl sulfate is destroyed
  2. additionby adding ammonia
  3. customThe product is precipitated
  4. temperatureby cooling
  5. filtrationfiltered off
  6. washwashed with water

Sources & evidence

ORD record
ord-1a377c485efd47a19c9ed3abf55a3c32
Source dataset
uspto-grants-1999_08
Patent number
US05945556

Reaction notes

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