Triethylamine → (3-Chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester

HRID 397192Notes

Reaction equation

HRID 397192 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:19]([Cl:27])[CH:18]=1)=[N:5][NH:6]S(C1C=CC(C)=CC=1)(=O)=O.C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3](=[O:28])[C:4]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:19]([Cl:27])[CH:18]=1)=[N+:5]=[N-:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86584878(3-Chloro-4-methanesulfonyl-phenyl)-(4-toluenesulfonyl-hydrazono)-acetic acid methyl ester

Product 1

HCID 86584876(3-Chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-chloro-4-methanesulfonyl-phenyl)-(4-toluenesulfonyl-hydrazono)-acetic acid methyl ester (3.82 g, 8.5 mmol) and triethylamine (1.3 mL, 9.35 mmol) in dichloromethane (40 mL) was stirred at 25° C. After 1 h, the reaction was evaporated under reduced pressure and the resulting residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) to give (3-chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester (978 mg, 40% yield) as a bright yellowish orange solid, mp 102.7-106.5° C.; EI-HRMS m/e calcd for C10H9N2ClSO4 (M+) 287.9972, found 287.9979.

Workup

  1. customthe reaction was evaporated under reduced pressure
  2. customthe resulting residue was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-00b55f5c17e842f587b01db2a099fb35
Source dataset
uspto-grants-2003_08
Patent number
US06608218B2

Reaction notes

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