Triethylamine → Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

HRID 242007

Reaction equation

HRID 242007 reaction equation
[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(NC1C=CC(S([N:37]=[N+:38]=[N-])(=O)=O)=CC=1)(=O)C>C(#N)C>[Cl:1][C:2]1[C:3]([F:16])=[C:4]([C:8](=[O:15])[C:9](=[N+:37]=[N-:38])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 51291854-Acetamidobenzenesulfonyl azideHCID 64717392Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 86659989Ethyl 3-(3-chloro-2-fluorophenyl)-2-diazo-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Ethyl 3-(3-chloro-2-fluorophenyl)-3-oxopropanoate (1.30 g, 5.31 mmol), triethylamine (0.618 g, 6.11 mmol, 1.15 equiv), and 4-acetamidobenzenesulfonyl azide (1.40 g, 5.85 mmol, 1.1 equiv) were combined in acetonitrile (15 mL). After stirred at ambient temperature for 30 minutes, the mixture was concentrated in vacuo and the residue was treated with sodium hydroxide (25 mL, 2 M aqueous) and extracted with twice chloroform. The combined organic extracts were washed once with brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate), providing the titled compound.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was treated with sodium hydroxide (25 mL, 2 M aqueous)
  3. extractionextracted with twice chloroform
  4. washThe combined organic extracts were washed once with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 40:60; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-85b62a5695854a139211369c4df8ff2b
Source dataset
uspto-grants-2014_02
Patent number
US08653079B2

Linked notes

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