Benzoyl chloride, 3-chloro- → 1-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanol

HRID 732040Notes

Reaction equation

HRID 732040 reaction equation
[OH:1][CH:2]([CH3:7])[C:3]([NH:5][OH:6])=[NH:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=O>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([C:12]2[O:6][N:5]=[C:3]([CH:2]([OH:1])[CH3:7])[N:4]=2)[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 5063567N',2-dihydroxypropanimidamide

Product 1

HCID 578379411-[5-(3-Chlorophenyl)-1,2,4-oxadiazol-3-yl]ethanolYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.19 g (30.6 mmol) 2,N-dihydroxy-propionamidine in 25 ml pyridine was added 4.3 ml (33.7 mmol) 3-chloro-benzoyl chloride at 0° C. Cooling was removed and the mixture was stirred at room temperature for 25 min and at reflux for 25 min. After cooling the mixture was poured into water and extracted twice with CH2Cl2. The organic phase was dried and concentrated. Recrystallization from heptane/EtOAc afforded 4.12 g (60%) of a white solid. 1H NMR (CDCl3), d (ppm): 1.68 (d, 3 H) 2.67 (m, 1 H) 5.09 (m, 1 H) 7.46 (t, 1 H) 7.56 (d, 1 H) 8.01 (d, 1 H) 8.13 (s, 1 H).

Workup

  1. temperatureCooling
  2. customwas removed
  3. temperatureat reflux for 25 min
  4. temperatureAfter cooling the mixture
  5. additionwas poured into water
  6. extractionextracted twice with CH2Cl2
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. customRecrystallization from heptane/EtOAc

Sources & evidence

ORD record
ord-b258066a0f9a4328b039ba4f779c16d4
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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