2-(Dimethylamino)benzenethiol → 3-(4-Chlorophenylthiomethyl)-5-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole

HRID 848115Notes

Reaction equation

HRID 848115 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].Cl[CH2:12][C:13]1[O:17][N:16]=[C:15]([CH2:18][S:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:14]=1>C[O-].[Na+].CO>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([S:19][CH2:18][C:15]2[N:14]=[C:13]([CH2:12][S:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[N:2]([CH3:10])[CH3:1])[O:17][N:16]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 52518512-(Dimethylamino)benzenethiolHCID 205663165-Chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole

Product 1

HCID 205663253-(4-Chlorophenylthiomethyl)-5-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

2-Dimethylaminobenzenethiol (1.67 g, 0.011 mol) was dissolved in a solution of sodium methoxide (0.59 g) in methanol (50 ml) and 5-chloromethyl-3-(4-chlorophenylthiomethyl)-1,2,4-oxadiazole (3.0 g 0.011 mol) was added dropwise with stirring. After a further 10 min. stirring the solution was filtered and evaporated to leave a brown oil, which was purified by chromatography on silica gel elution with hexane/ether (3:2) giving 3-(4-chlorophenylthiomethyl)-5-(2-dimethylaminophenylthiomethyl)-1,2,4-oxadiazole as a colourless oil, mass spectrum M+1 392; refractive index 1.6263.

Workup

  1. additionwas added dropwise
  2. stirringAfter a further 10 min. stirring the solution
  3. filtrationwas filtered
  4. customevaporated
  5. customto leave a brown oil, which
  6. customwas purified by chromatography on silica gel elution with hexane/ether (3:2)

Sources & evidence

ORD record
ord-72da56557c4e456ab34dea5da02c4f35
Source dataset
uspto-grants-1981_10
Patent number
US04294842

Reaction notes

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