Triethylamine → Ethyl 2-diazo-3-(2,6-difluorophenyl)-3-oxopropanoate

HRID 449946Notes

Reaction equation

HRID 449946 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(N(CC)CC)C.C(NC1C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[N+:37](=[C:10]([C:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 51291854-Acetamidobenzenesulfonyl azideHCID 13550002Ethyl 3-(2,6-difluorophenyl)-3-oxopropanoate

Product 1

HCID 86681842Ethyl 2-diazo-3-(2,6-difluorophenyl)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 3-(2,6-difluorophenyl)-3-oxopropanoate (12.3 g, 53.8 mmol) and triethylamine (22.5 mL, 0.161 mol, 3.0 equiv) were dissolved in acetonitrile (160 mL) and treated with 4-acetamidobenzenesulfonyl azide. The mixture was stirred for 18 hours at ambient temperature, concentrated in vacuo and the residue was purified by silica gel chromatography (eluting with chloroform), providing the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue was purified by silica gel chromatography (eluting with chloroform)

Sources & evidence

ORD record
ord-99c4e7853a2044faa26b6d908acfbd65
Source dataset
uspto-grants-2013_07
Patent number
US08486946B2

Reaction notes

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