Chlorine → 2,6-Dichlorobenzoxazole

HRID 1388769Notes

Reaction equation

HRID 1388769 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](S)[O:8][C:4]=2[CH:3]=1.[K].[Cl:13]Cl>ClC1C=CC=CC=1>[Cl:13][C:7]1[O:8][C:4]2[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 178527789HCID 178527789, compound

Product 1

HCID 771752,6-DichlorobenzoxazoleYield 91%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

223.5 g (1 mole) of potassium 6-chloro-2-mercaptobenzoxazole are suspended in 500 ml of chlorobenzene and 180 g (2.5 moles) of chlorine gas are added in the course of 3 hours at a temperature of approx. 25° C. Stirring is continued for 12 hours at room temperature and excess chlorine is blown out of the mixture by means of nitrogen. The precipitated potassium chloride is filtered off and rinsed with approx. 200 ml of chlorobenzene. The filtrate is then distilled. When the sulfur dichloride and chlorobenzene have been distilled off, 171 g (91% of theory) of 2,6-dichlorobenzoxazole are obtained, having a melting point of 49°-51° C. and a boiling point of 124°-128.5° C. under approx. 25 mbars.

Workup

  1. filtrationThe precipitated potassium chloride is filtered off
  2. washrinsed with approx. 200 ml of chlorobenzene
  3. distillationThe filtrate is then distilled
  4. distillationWhen the sulfur dichloride and chlorobenzene have been distilled off

Sources & evidence

ORD record
ord-94db8eb85b864b91bb0049fbabe2ea0e
Source dataset
uspto-grants-1984_02
Patent number
US04433153

Reaction notes

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