Diethyl Sulfate → HCID 2725502, compound

HRID 1929283Notes

Reaction equation

HRID 1929283 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].S(OCC)(O[CH2:25][CH3:26])(=O)=O>CN(C=O)C>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:8]([O:10][CH2:25][CH3:26])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 12383395HCID 12383395, compound

Product 1

HCID 2725502HCID 2725502, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 g (562 mmol) of 3-acetamido-4-chlorobenzoic acid were dissolved in 77 ml of DMF and stirred with 93.16 g (674 mmol) of potassium carbonate at 60° C. for 30 min. The mixture was then cooled, admixed with 91 g (590 mmol) of diethyl sulfate, and left with stirring at RT for 7 h. The batch was concentrated, the residue was stirred with 2 l of water, and the precipitated crystals were isolated by filtration with suction. They were washed with water and dried in a vacuum cabinet at 70° C. for 3 h.

Workup

  1. temperatureThe mixture was then cooled
  2. waitleft
  3. concentrationThe batch was concentrated
  4. stirringthe residue was stirred with 2 l of water
  5. customthe precipitated crystals were isolated by filtration with suction
  6. washThey were washed with water
  7. customdried in a vacuum cabinet at 70° C. for 3 h.

Sources & evidence

ORD record
ord-9408eea6c6904a4bb519398eec17ccfa
Source dataset
uspto-grants-2012_05
Patent number
US08188002B2

Reaction notes

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