Water → HCID 18188006, compound

HRID 2200851Notes

Reaction equation

HRID 2200851 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([NH:11][C:12]2[C:13]([Cl:19])=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])=[C:5]([CH2:7][C:8]([O-:10])=[O:9])[CH:6]=1.[Na+].O.C(=O)(O)[O-].[Na+].S(Cl)(O[CH2:31][Cl:32])(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[NH:11][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH2:7][C:8]([O:10][CH2:31][Cl:32])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfateHCID 5018304Diclofenac sodium

Product 1

HCID 18188006HCID 18188006, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Diclofenac sodium [331] (0.1 g, 0.33 mmol, 1.0 eq) DCM (2 ml), water (2 ml), sodium bicarbonate (0.105 g, 0.125 mmol, 3.81 eq) and tetrabutylammonium hydrogen sulfate (0.011 g, 0.033 mmol, 0.1 eq) were stirred at 25° C. for 2 min. A solution of chloromethyl chlorosulfate [323] (0.06 g, 0.363 mmol, 1.1 eq) in DCM (1 ml) was added dropwise. This biphasic system was stirred at RT for 1 h. The organic layer was separated and dried over anhydrous Na2SO4. Evaporation of the solvent under vacuum gave the product as a white solid, chloromethyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate [332] (0.11 g, 95%)

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. customEvaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-3fcae7b4e27b4e819308d39e7aa87168
Source dataset
uspto-grants-2016_06
Patent number
US09359376B2

Reaction notes

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