Water → HCID 63379806, compound

HRID 58618Notes

Reaction equation

HRID 58618 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[NH2:12][C:13](=[N:19]O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)C(C)C)(C)C.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[O:10][N:19]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 906924-Chlorophenylacetyl chlorideHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 63379806HCID 63379806, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-chlorophenyl)acetyl chloride (0.554 mL; 3.78 mmol) was added to a mixture of ethyl 2-amino-2-(hydroxyimino)acetate (0.5 g; 3.78 mmol) and N,N diisopropylethylamine (1.05 mL; 6.06 mmol) in dichloromethane (15 mL) at −15° C. The reaction mixture was stirred at room temperature overnight and poured into a mixture of ice and water. The formed precipitate was filtered off, suspended in pyridine (18 mL) and refluxed in a sealed tube for 20 h and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica (eluent to 100% ethyl acetate in heptane) to yield 0.506 g (50%) of ethyl 5-(4-chlorobenzyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

Workup

  1. filtrationThe formed precipitate was filtered off
  2. temperaturerefluxed in a sealed tube for 20 h
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography on silica (eluent to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-4852a0a5bbfe44b8a55402e9c2cc281b
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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