Thiabendazole → HCID 54134584, compound

HRID 328340Notes

Reaction equation

HRID 328340 reaction equation
[CH2:1]([C:9](Cl)=[S:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[S:12]1[CH:16]=[C:15]([C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)[N:14]=[CH:13]1>N1C=CC=CC=1>[CH2:1]([C:9]([N:21]1[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[N:18]=[C:17]1[C:15]1[N:14]=[CH:13][S:12][CH:16]=1)=[S:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 5430ThiabendazoleHCID 54550885HCID 54550885, compound

Product 1

HCID 54134584HCID 54134584, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

249 G. (1.19 moles) of n-octylthiocarbonyl chloride is added dropwise over a period of 20 minutes to a stirred suspension of 240 g. (1.19 moles) of 2-(4-thiazolyl)-benzimidazole and 2400 ml. of pyridine; a slight heat rise is evidenced. The reaction mixture is stirred at room temperature for 19 hours, filtered and the solid material washed with methylene chloride. The combined filtrate and washings are evaporated to dryness in vacuo. The residue is mixed with 2000 ml. of methylene chloride and filtered. The solid material is washed with methylene chloride and the combined filtrate and washing are wased twice with water, 3 times with cold 0.25 normal hydrochloric acid (5000 ml. total volume), once with saturated cold sodium bicarbonate and twice with water. The methylene chloride is dried, evaporated to dryness in vacuo affording a syrupy oil which crystallizes under vacuum. The solid material is dissolved in 3 liters of hexane and filtered and the hexane evaporated to a small volume and diluted with petroleum ether to a volume of 3000 ml. whereupon crystallization results. The solid material is filtered and washed with cold petroleum ether affording 219.8 g. (54%) of pure 1-n-octylthiocarbonyl-2-(4-thiazolyl)-benzimidazole, melting point 58° to 59° C.

Workup

  1. filtrationfiltered
  2. washthe solid material washed with methylene chloride
  3. customThe combined filtrate and washings are evaporated to dryness in vacuo
  4. additionThe residue is mixed with 2000 ml
  5. filtrationof methylene chloride and filtered
  6. washThe solid material is washed with methylene chloride
  7. washthe combined filtrate and washing
  8. dry with materialThe methylene chloride is dried
  9. customevaporated to dryness in vacuo
  10. customaffording a syrupy oil which
  11. customcrystallizes under vacuum
  12. dissolutionThe solid material is dissolved in 3 liters of hexane
  13. filtrationfiltered
  14. customthe hexane evaporated to a small volume
  15. additiondiluted with petroleum ether to a volume of 3000 ml
  16. customwhereupon crystallization
  17. customresults
  18. filtrationThe solid material is filtered
  19. washwashed with cold petroleum ether affording 219.8 g

Sources & evidence

ORD record
ord-d848ee4552e5452bb1964e1c5c1d1f2c
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Reaction notes

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