Benzene → HCID 18332472, compound

HRID 1739386Notes

Reaction equation

HRID 1739386 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([O:19][CH3:20])[C:15]([NH:17][NH2:18])=[O:16])=[C:4]([CH3:23])[CH:3]=1.[CH:24]([O-])([O-])OCC.C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([C:15]2[O:16][CH:24]=[N:18][N:17]=2)[O:19][CH3:20])=[C:4]([CH3:23])[CH:3]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 53630039EthylorthoformateHCID 69948306HCID 69948306, compound

Product 1

HCID 18332472HCID 18332472, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 0.50 g (1.5 mmol) of 2-(4-chloro-2-methylphenoxymethyl)phenyl-2-methoxyacetic acid hydrazide was added 1.5 ml of ethyl orthoformate, stirred under reflux for 3 hours, and thereafter concentrated under reduced pressure. To the residue thus obtained, 4.5 ml of benzene and 0.03 g (0.15 mmol) of p-toluenesulfonic acid monohydrate were added and stirred under reflux for an hour. After completion of the reaction, 100 ml of water was added and extracted twice with 50 ml of dichloromethane. The dichloromethane layer was dried over anhydrous magnesium and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane) to give 2-[2-(4-chloro-2-methylphenoxymethyl)-α-methoxybenzyl]-1,3,4-oxadiazole (0.07 g, 13.5%) as colorless crystals. mp. 68-70° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated under reduced pressure
  3. customTo the residue thus obtained
  4. stirringstirred
  5. temperatureunder reflux for an hour
  6. additionwas added
  7. extractionextracted twice with 50 ml of dichloromethane
  8. dry with materialThe dichloromethane layer was dried over anhydrous magnesium
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-1ea809d7d51646218e557dd32611fa98
Source dataset
uspto-grants-1999_10
Patent number
US05965740

Reaction notes

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