Methanesulfonyl chloride → HCID 70817767, compound

HRID 82291Notes

Reaction equation

HRID 82291 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH3:13])=[CH:8][CH:7]=1)[CH3:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]([S:16]([CH3:15])(=[O:18])=[O:17])[CH3:13])=[CH:8][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11550151N-methyl-4-ethoxycarbonylmethylaniline

Product 1

HCID 70817767HCID 70817767, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of (4-methylamino-phenyl)-acetic acid ethyl ester (Preparation 269, 418 mg, 2.16 mmol) in pyridine (4 mL) was added methanesulfonyl chloride (0.25 mL, 3.24 mmol) and the mixture stirred at room temperature for 3 hours. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc (3×15 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), dried (Na2SO4) and evaporated in vacuo to afford the title compound as a gum in 78% yield, 460 mg.

Workup

  1. customThe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with EtOAc (3×15 mL)
  3. washThe combined organic layers were washed with water (10 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-bc1380e2fc3e468d9496902d7459cadf
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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