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

HRID 328341Notes

Reaction equation

HRID 328341 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:3].[S:17]1[CH:21]=[C:20]([C:22]2[NH:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[N:19]=[CH:18]1>N1C=CC=CC=1>[CH:6]1([CH2:5][O:4][C:2]([N:26]2[C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]=[C:22]2[C:20]2[N:19]=[CH:18][S:17][CH:21]=2)=[O:3])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 5430ThiabendazoleHCID 21441774Cycloundecylmethyl chloroformate

Product 1

HCID 214417641-Cycloundecylmethoxycarbonyl-2-(4-thiazolyl)-benzimidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20.3 G. (0.082 moles) of cycloundecylmethyl chloroformate is added dropwise at room temperature to 16.4 g. (0.082 moles) of 2-(4-thiazolyl)-benzimidazole suspended in 200 ml. of pyridine. The temperature rises spontaneously to 35° C and the reaction mixture is then stirred overnight at room temperature, filtered and the filtrate evaporated to dryness in vacuo. The residue is treated with methylene chloride and washed 3 times with 2.5N hydrochloric acid and twice with water. The methylene chloride is treated with charcoal, filtered and evaporated to dryness in vacuo affording 25 g. of an oil which solidifies on standing and is recrystallized from hexane affording 20 g. of 1-cycloundecylmethoxycarbonyl-2-(4-thiazolyl)-benzimidazole, melting point 86° to 87° C.

Workup

  1. customrises spontaneously to 35° C
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness in vacuo
  4. additionThe residue is treated with methylene chloride
  5. washwashed 3 times with 2.5N hydrochloric acid
  6. additionThe methylene chloride is treated with charcoal
  7. filtrationfiltered
  8. customevaporated to dryness in vacuo
  9. customaffording 25 g
  10. customis recrystallized from hexane affording 20 g

Sources & evidence

ORD record
ord-8e940d2769f54ffc971e4d237cecde32
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Reaction notes

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