Oxalyl chloride → HCID 63379767, compound

HRID 1918633Notes

Reaction equation

HRID 1918633 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[NH2:18][C:19](=[N:25]O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]1[O:6][N:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:18]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 763392,5-Difluorobenzoic acidHCID 81531DiisopropylethylamineHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 63379767HCID 63379767, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

This compound was prepared according to general method 2 with (step I) 2,5-difluorobenzoic acid (0.299 g; 1.89 mmol) and oxalyl chloride (0.176 mL; 2.08 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.250 g; 1.89 mmol) and N,N diisopropylethylamine (0.527 mL; 3.03 mmol) in dichloromethane (10 mL) and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.172 g (36%) of ethyl 5-(2,5-difluorophenyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b734849372c0457fa7156aca76532d70
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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