Oxalyl chloride → Ethyl 5-(3,4-dichlorobenzyl)-1,2,4-oxadiazole-3-carboxylate

HRID 58616

Reaction equation

HRID 58616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C(Cl)(=O)C(Cl)=O.[NH2:19][C:20](=[N:26]O)[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)C(C)C)(C)C>ClCCl.N1C=CC=CC=1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[CH2:9][C:10]1[O:12][N:26]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:19]=1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 798743,4-Dichlorophenylacetic acidHCID 81531DiisopropylethylamineHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 63379228Ethyl 5-(3,4-dichlorobenzyl)-1,2,4-oxadiazole-3-carboxylateYield 18%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

This compound was prepared according to general method 2 with (step I) 2-(3,4-dichlorophenyl)acetic acid (0.775 g; 3.78 mmol) and oxalyl chloride (0.352 mL; 4.16 mmol) in dichloromethane (8 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino)acetate (0.500 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 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 0.2004 g (18%) of ethyl 5-(3,4-dichlorobenzyl)-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-7f00e48486d44ba39c45069519aedbf1
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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