Thiabendazole → 1-Benzylthiocarbonyl-2-(4-thiazolyl)-benzimidazole

HRID 328338

Reaction equation

HRID 328338 reaction equation
[CH2:1]([C:8](Cl)=[S:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:11]1[CH:15]=[C:14]([C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[N:13]=[CH:12]1>N1C=CC=CC=1>[CH2:1]([C:8]([N:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=[C:16]1[C:14]1[N:13]=[CH:12][S:11][CH:15]=1)=[S:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5430ThiabendazoleHCID 19906501HCID 19906501, compound

Product 1

HCID 540529801-Benzylthiocarbonyl-2-(4-thiazolyl)-benzimidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

17.0 G. (0.091 moles) of benzylthiocarbonyl chloride is added dropwise under anhydrous conditions over a period of 25 minutes to a stirred suspension of 18.3 g. (0.091 moles) of 2-(4-thiazolyl)-benzimidazole in 140 ml. of pyridine. All of the solid material dissolved before the completion of the addition. When the addition is complete, precipitation of pyridine hydrochloride commences. The reaction mixture is stirred at room temperature for 18 hours, filtered and the pyridine solution evaporated to dryness in vacuo. The residue is dissolved in 250 ml. of methylene chloride filtered and the filtrate washed twice with 250 ml. of 0.25 normal hydrochloric acid and 200 ml. of saturated sodium bicarbonate solution. The methylene chloride is dried, treated with charcoal, filtered and evaporated to dryness in vacuo affording a solid material which is recrystallized from toluene affording 14.3 g. (45%) of 1-benzylthiocarbonyl-2-(4-thiazolyl)-benzimidazole, melting point 122° to 123° C.

Workup

  1. dissolutionAll of the solid material dissolved before the completion of the addition
  2. additionWhen the addition
  3. customprecipitation of pyridine hydrochloride commences
  4. filtrationfiltered
  5. customthe pyridine solution evaporated to dryness in vacuo
  6. dissolutionThe residue is dissolved in 250 ml
  7. filtrationof methylene chloride filtered
  8. washthe filtrate washed twice with 250 ml
  9. dry with materialThe methylene chloride is dried
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. customevaporated to dryness in vacuo
  13. customaffording a solid material which
  14. customis recrystallized from toluene affording 14.3 g

Sources & evidence

ORD record
ord-b31944e15c4d4e3e84661abbfc3d4d7e
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Linked notes

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