2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane methanesulphonate → 1-[2-(2,4-Dichlorophenyl)-2-hydroxy-3-(thiazol-2-ylthio)propyl]-1,2,4-triazole

HRID 2118492Notes

Reaction equation

HRID 2118492 reaction equation
CS(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:16][O:15]1.[SH:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1>C(O)(=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]([OH:15])([CH2:16][S:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1)[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

4

Reactant 2

HCID 867396002-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane methanesulphonateHCID 178527881HCID 178527881, compound

Product 1

HCID 201939471-[2-(2,4-Dichlorophenyl)-2-hydroxy-3-(thiazol-2-ylthio)propyl]-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane, methanesulphonate salt, (6 g, 0.0164 m) and 2-mercaptothiazole (6 g, 0.05 m) were heated in glacial acetic acid (200 ml) under refluxed for 4 hours. The solvent was then evaporated and the residue was basified with dilute sodium hydroxide solution and extracted with methylene chloride. The extract was washed once with dilute sodium hydroxide solution, dried (MgSO4) and evaporated to give a pale brown glass (5.4 g) which was chromatographed on silica, eluting with ethyl acetate:ether:methanol:diethylamine 25:75:2:2, to give, after one recrystallization from isopropanol, the title compound 2 g, (32%); m.p. 110°-111° C.

Workup

  1. temperatureunder refluxed for 4 hours
  2. customThe solvent was then evaporated
  3. extractionextracted with methylene chloride
  4. washThe extract was washed once with dilute sodium hydroxide solution
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-6881f6dad1104d698232e5bf2ccb8b7f
Source dataset
uspto-grants-1987_07
Patent number
US04678789

Reaction notes

Loading…