Chloroacetyl chloride → 5-Chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole

HRID 848114Notes

Reaction equation

HRID 848114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10](=[N:12][OH:13])[NH2:11])=[CH:4][CH:3]=1.[Cl:14][CH2:15][C:16](Cl)=O>C1(C)C=CC=CC=1>[Cl:14][CH2:15][C:16]1[O:13][N:12]=[C:10]([CH2:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:11]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 30395982-(4-Chlorophenylthio)acetamidoxime

Product 1

HCID 205663165-Chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2-(4-Chlorophenylthio)acetamidoxime (21.7 g, 0.1 mol) was stirred in toluene (150 ml) whilst a solution of chloroacetyl chloride (11.3 g, 0.1 mol) in toluene (50 ml) was added dropwise over 20 minutes. The thick suspension was refluxed for 1 hour to give a black mixture which was cooled and then extracted with water and ether. The ether extracts were evaporated to give a brown oil which was chromatographed on silica gel (200 g) and eluted with ether/hexane (2:3) to give 5-chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole.

Workup

  1. additionwas added dropwise over 20 minutes
  2. temperatureThe thick suspension was refluxed for 1 hour
  3. customto give a black mixture which
  4. temperaturewas cooled
  5. extractionextracted with water and ether
  6. customThe ether extracts were evaporated
  7. customto give a brown oil which
  8. customwas chromatographed on silica gel (200 g)
  9. washeluted with ether/hexane (2:3)

Sources & evidence

ORD record
ord-8bc5b6dcf1274343ba0f68ccfd92fe99
Source dataset
uspto-grants-1981_10
Patent number
US04294842

Reaction notes

Loading…