Phosphorus pentachloride → 2-Chloro-6-methoxy-1,3-benzoxazole

HRID 1780674Notes

Reaction equation

HRID 1780674 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8](S)[O:9][C:5]=2[CH:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:14]>ClC1C=CC=CC=1>[Cl:14][C:8]1[O:9][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 178488033HCID 178488033, compound

Product 1

HCID 106790422-Chloro-6-methoxy-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A 100 mg portion of 6-methoxy-2-mercaptobenzoxazole and 172 mg of phosphorus pentachloride were dissolved in 35 ml of chlorobenzene to carry out 8 hours of heating under reflux. The reaction solution was poured into 300 ml of ice water and extracted three times with 100 ml of dichloromethane. The resulting organic layers were combined, dehydrated with sodium sulfate, concentrated under a reduced pressure and then purified by a silica gel column chromatography (n-hexane:chloroform=1:1), to obtain 79 mg of 2-chloro-6-methoxybenzoxazole.

Workup

  1. temperatureof heating
  2. temperatureunder reflux
  3. extractionextracted three times with 100 ml of dichloromethane
  4. concentrationconcentrated under a reduced pressure
  5. custompurified by a silica gel column chromatography (n-hexane:chloroform=1:1)

Sources & evidence

ORD record
ord-cab473e0a45948e4a1443e38124b838e
Source dataset
uspto-grants-1997_05
Patent number
US05631257

Reaction notes

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