Thiabendazole → HCID 11481606, compound

HRID 1471225Notes

Reaction equation

HRID 1471225 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:9]=[C:8]([C:10]3[N:14]=[CH:13][S:12][CH:11]=3)[NH:7][C:5]=2[CH:6]=1.[OH-].[Na+].[CH2:17](OS(OCC)(=O)=O)[CH3:18]>O1CCCC1>[CH2:17]([N:9]1[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=2[N:7]=[C:8]1[C:10]1[N:14]=[CH:13][S:12][CH:11]=1)[CH3:18]

Participants

5

Reactant 3

HCID 5430ThiabendazoleHCID 6163Diethyl SulfateHCID 14798Sodium Hydroxide

Product 1

HCID 11481606HCID 11481606, compoundYield 64.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.0 g Thiabendazole and 1.31 g sodium hydroxide were added to 40 ml of tetrahydrofuran. The white slurry was stirred under nitrogen and 4.6 g of diethylsulfate was added dropwise. The mixture was stirred at 50 C for 16 hours. The mixture was quenched with 75 ml of water and then extracted with 75 ml or ethyl acetate. The organic layer was washed with 15 ml of water. Following solvent removal, an off-white solid crystallized. The solid was recrystallized from 30 ml (2:1, v/v) ethanol/water. The solid was dried under vacuum for 3 hrs at 50 C. 3.7 g of a white solid was obtained.

Workup

  1. stirringThe mixture was stirred at 50 C for 16 hours
  2. customThe mixture was quenched with 75 ml of water
  3. extractionextracted with 75 ml or ethyl acetate
  4. washThe organic layer was washed with 15 ml of water
  5. customFollowing solvent removal
  6. customan off-white solid crystallized
  7. customThe solid was recrystallized from 30 ml (2:1, v/v) ethanol/water
  8. customThe solid was dried under vacuum for 3 hrs at 50 C

Sources & evidence

ORD record
ord-f731b1a1e17e42e9ae73b6a35e354ba8
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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