Thiabendazole → 1-(3-Hexyloxycarbonyl)-2-(4-thiazolyl)-benzimidazole

HRID 328335

Reaction equation

HRID 328335 reaction equation
Cl[C:2]([O:4][CH:5]([CH2:8][CH2:9][CH3:10])[CH2:6][CH3:7])=[O:3].[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>[CH3:7][CH2:6][CH:5]([O:4][C:2]([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)=[O:3])[CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 5430ThiabendazoleHCID 54555278Hexan-3-yl carbonochloridate2×

Product 1

HCID 540368021-(3-Hexyloxycarbonyl)-2-(4-thiazolyl)-benzimidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

28.3 G. (0.172 moles) of 3-hexyl chloroformate is added dropwise with protection from moisture to a stirred suspension of 33.1 g. (0.165 moles) of 2-(4-thiazolyl)-benzimidazole in 200 ml. of anhydrous pyridine. The 3-hexyl chloroformate is added over a period of 20 minutes during which time the reaction mixture initially becomes a clear solution followed by the precipitation of pyridine hydrochloride. The reaction mixture is stirred overnight at room temperature filtered to remove pyridine hydrochloride which is washed with some additional anhydrous pyridine and the combined filtrates and washings evaporated to dryness in vacuo. An oil is obtained which is dissolved in 300 ml. of methylene chloride and filtered. The filtrate is washed twice with a 250 ml. of 0.25 N-hydrochloric acid containing ice followed by a washing with 200 ml. of saturated sodium bicarbonate solution. The methylenechloride is dried, treated with charcoal, filtered and evaporated to dryness in vacuo affording 39.2 g. of an orange oil which solidified on standing. The solid material is recrystallized from hexane affording 33.5 g. (62%) of 1-(3-hexyloxycarbonyl)-2-(4-thiazolyl)-benzimidazole melting point 79.5 to 81° C.

Workup

  1. customfollowed by the precipitation of pyridine hydrochloride
  2. filtrationfiltered
  3. customto remove pyridine hydrochloride which
  4. washis washed with some additional anhydrous pyridine
  5. customthe combined filtrates and washings evaporated to dryness in vacuo
  6. customAn oil is obtained which
  7. dissolutionis dissolved in 300 ml
  8. filtrationof methylene chloride and filtered
  9. washThe filtrate is washed twice with a 250 ml
  10. additionof 0.25 N-hydrochloric acid containing ice
  11. dry with materialThe methylenechloride is dried
  12. additiontreated with charcoal
  13. filtrationfiltered
  14. customevaporated to dryness in vacuo
  15. customaffording 39.2 g
  16. customThe solid material is recrystallized from hexane affording 33.5 g

Sources & evidence

ORD record
ord-69128df4613f4c9ea1e7da12e5aa9982
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Linked notes

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