Thiabendazole → HCID 21441751, compound

HRID 328339Notes

Reaction equation

HRID 328339 reaction equation
Cl[C:2]([O:4][CH2:5][CH2:6][CH:7]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:8])=[O:3].[S:15]1[CH:19]=[C:18]([C:20]2[NH:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[N:17]=[CH:16]1>N1C=CC=CC=1>[CH2:5]([O:4][C:2]([N:24]1[C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[N:21]=[C:20]1[C:18]1[N:17]=[CH:16][S:15][CH:19]=1)=[O:3])[CH2:6][CH:7]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH3:8]

Participants

4

Reactant 2

HCID 5430ThiabendazoleHCID 185209753,7-Dimethyloct-6-en-1-yl carbonochloridate

Product 1

HCID 21441751HCID 21441751, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

11.0 Grams (0.05 moles) of citronellyl chloroformate is added over a period of 1/2 hour to a stirred suspension of 10 grams (0.05 moles) of 2-(4-thiazolyl)benzimidazole and 75 ml. of pyridine at room temperature. The reaction mixture is stirred overnight at room temperature protected from moisture. The solid material is filtered, washed with pryidine and the filtrate and washings evaporated to dryness in vacuo. The residue is dissolved in methylene chloride and the solution washed successively with dilute cold hydrochloric acid, cold water, cold dilute sodium bicarbonate solution and water. The methylene chloride is dried, evaporated to dryness in vacuo affording 16.6 grams of a viscous oil. The oil is chromatographed on a column of silica gel eluting with hexane affording 14.6 grams (76%) of an oil which thin layer chromatography reveals to be pure material and which analyzes as 1-citronellyloxycarbonyl-2-(4-thiazolyl)benzimidazole.

Workup

  1. customat room temperature
  2. filtrationThe solid material is filtered
  3. washwashed with pryidine
  4. customthe filtrate and washings evaporated to dryness in vacuo
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washthe solution washed successively
  7. additionwith dilute cold hydrochloric acid, cold water, cold dilute sodium bicarbonate solution and water
  8. dry with materialThe methylene chloride is dried
  9. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-2205d1f6cbe2457d89d577609226fe36
Source dataset
uspto-grants-1977_04
Patent number
US04017505

Reaction notes

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