Water → HCID 14369975, compound

HRID 1381510Notes

Reaction equation

HRID 1381510 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:4])=[O:3].[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.ClCCl>[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 11430Potassium CarbonateHCID 14369974HCID 14369974, compound

Product 1

HCID 14369975HCID 14369975, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(methylsulfonylamino)phenylacetate (2.00 kg) in dimethylformamide (10 l), under an atmosphere of nitrogen, is added 4-chlorobenzyl chloride (1.37 kg) all at once, followed by anhydrous potassium carbonate (1.18 kg). The mixture is heated at 75° and stirred for 4 hours, then cooled to room temperature overnight at which time it is poured into water (50 l). The resulting precipitate is dissolved in dichloromethane (4 l). The dichloromethane solution is washed with brine (500 ml), dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated in vacuo to give a solid which is air-dried overnight and vacuum-dried (0.3 mm Hg) at room temperature to yield methyl 2-[N-(4-chlorophenylmethyl)-methylsulfonylamino]phenylacetate mp 73°-75°.

Workup

  1. temperatureThe mixture is heated at 75°
  2. washThe dichloromethane solution is washed with brine (500 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate is evaporated in vacuo
  6. customto give a solid which
  7. customis air-dried overnight
  8. customvacuum-dried (0.3 mm Hg) at room temperature

Sources & evidence

ORD record
ord-58f0def98dc1480bb36027636f2d9bfc
Source dataset
uspto-grants-1989_02
Patent number
US04803197

Reaction notes

Loading…