Benzene → 3-Chloromethyl-5-phenoxy-(1,2,4)-thiadiazole

HRID 615922Notes

Reaction equation

HRID 615922 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O-:7])=[CH:3][CH:2]=1.[Na+].C1C=CC=CC=1.CN(C)C=O.[Cl:20][CH2:21][C:22]1[N:26]=[C:25](Cl)[S:24][N:23]=1>O>[Cl:20][CH2:21][C:22]1[N:26]=[C:25]([O:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)[S:24][N:23]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazoleHCID 4445035Phenolate Sodium

Product 1

HCID 131061443-Chloromethyl-5-phenoxy-(1,2,4)-thiadiazoleYield 63.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

5.8 g of sodium phenate were added to a mixture of 50 ml of benzene, 10 ml of dimethylformamide and 8.5 g of 3-chloromethyl-5-chloro-[1,2,4]-thiadiazole and the mixture was stirred at 20° C. for 24 hours. 50 ml of water were added to the mixture and the decanted aqueous phase was extracted with benzene. The combined organic phase was dried and evaporated to dryness. The oil residue was distilled under reduced pressure to obtain 7.2 g of 3-chloromethyl-5-phenoxy-[1,2,4]-thiadiazole boiling at 114°-116° C. at 0.5 mm Hg.

Workup

  1. extractionthe decanted aqueous phase was extracted with benzene
  2. customThe combined organic phase was dried
  3. customevaporated to dryness
  4. distillationThe oil residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5a216c6138884c4ab8d0a6230a5fc385
Source dataset
uspto-grants-1985_02
Patent number
US04501894

Reaction notes

Loading…