4-Chloro-2-methylbenzaldehyde → HCID 178426098, compound

HRID 589294Notes

Reaction equation

HRID 589294 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1.O[N:12]=[C:13]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)[NH2:14]>N1CCCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:7][N:12]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[NH:14]2)=[C:4]([CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 27576584-Chloro-2-methylbenzaldehydeHCID 303962450892-99-4

Product 1

HCID 178426098HCID 178426098, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 8082PiperidineCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-methylbenzaldehyde (229 mg, 1.49 mmol), N′-hydroxyfuran-2-carboximidamide (263 mg, 2.1 mmol) and one drop of piperidine was heated to 100° C. for 4 h. It was cooled to RT and purified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate) to give the 5-(4-chloro-2-methylphenyl)-3-(furan-2-yl)-4,5-dihydro-1,2,4-oxadiazole product (94 mg, 0.36 mmol) as an off-white solid with an HPLC purity 99%. The overall yield was approximately 24%. LC-MS [M+H] 263 (C13H11ClN2O2+H, expected 263.05).

Workup

  1. temperatureIt was cooled to RT
  2. custompurified by automated column chromatography on the ISCO-companion (SiO2, gradient heptane/ethyl acetate)

Sources & evidence

ORD record
ord-4a02c66c97754af5ba6502922c5018d3
Source dataset
uspto-grants-2016_01
Patent number
US09232800B2

Reaction notes

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