Triethylamine → Methyl 2-diazo-2-(3,4-dichlorophenyl)acetate

HRID 1019194Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:25])[C:4]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[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:25])[C:4](=[N+:5]=[N-:6])[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In a dry flask under argon was placed a solution of (3,4-dichloro-phenyl)-(4-toluenesulfonylhydrazono)-acetic acid methyl ester (1.45 g, 3.61 mmol) in dichloromethane (20 mL) containing triethylamine (0.55 mL, 3.97 mmol) at 25° C. The bright yellow solution was then stirred at 25° C. for 1 h, then the solvent was removed in vacuo to yield a bright yellow solid. The product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 7/1/0.5 hexanes/dichloromethane/methanol) to furnish diazo-(3,4-dichloro-phenyl)-acetic acid methyl ester (814 mg, 92% yield) as a bright yellowish orange solid: EI-HRMS m/e calcd for C9H6Cl2N2O2 (M+) 243.9806, found 243.9800.

Workup

customIn a dry flask under argon was placed
customthe solvent was removed in vacuo
customto yield a bright yellow solid
customThe product was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 7/1/0.5 hexanes/dichloromethane/methanol)

Sources & evidence

ORD record: ord-f7312034c7be47b0938fb46beaee7236
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06486184B2

Reaction notes

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