Pyridine → Methyl [2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]acetate

HRID 743983Notes

Reaction equation

HRID 743983 reaction equation
Cl[S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([O:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:22]=2[NH2:23])[N:13]=1.N1C=CC=CC=1>ClCCl>[CH3:19][O:18][C:16]1[CH:17]=[C:12]([O:11][CH3:10])[N:13]=[C:14]([O:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:22]=2[NH:23][S:2]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])=[O:3])[N:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11435213Methyl (chlorosulfonyl)acetateHCID 543689482-(4,6-Dimethoxypyrimidin-2-yloxy)-6-fluoroaniline

Product 1

HCID 54135497Methyl [2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluorophenylsulfamoyl]acetateYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl (chlorosulfonyl)acetate (13.0 g) in dichloromethane (20 ml) was added dropwise with stirring and cooling to 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-fluoroaniline (20 g) and pyridine (6.3 g) in dichloromethane (120 ml). After stirring for 2 hours, the mixture was allowed to stand at room temperature overnight. Washing with dilute hydrochloric acid and water, drying over magnesium sulfate, and running down, gave an oil which was triturated with ether. The resulting off-white solid was separated by filtration to give 20.4 g of the desired product, mp 111°-114° C.

Workup

  1. stirringAfter stirring for 2 hours
  2. washWashing with dilute hydrochloric acid and water
  3. dry with materialdrying over magnesium sulfate
  4. customgave an oil which
  5. customwas triturated with ether
  6. customThe resulting off-white solid was separated by filtration

Sources & evidence

ORD record
ord-f4ed29c5f03642218d05b699f3c346f7
Source dataset
uspto-grants-1996_09
Patent number
US05559081

Reaction notes

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