Triethylamine → Luxabendazole

HRID 980848Notes

Reaction equation

HRID 980848 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[CH:22]=[CH:21][C:12]2[N:13]=[C:14]([NH:16][C:17]([O:19][CH3:20])=[O:18])[NH:15][C:11]=2[CH:10]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(O)(=O)C>[F:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:8][C:9]2[CH:22]=[CH:21][C:12]3[N:13]=[C:14]([NH:16][C:17]([O:19][CH3:20])=[O:18])[NH:15][C:11]=3[CH:10]=2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 115152Methyl 5-hydroxybenzimidazol-2-ylcarbamate

Product 1

HCID 72019Luxabendazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.8 ml of triethylamine are added dropwise, with stirring, to 2.07 g of methyl 5-hydroxybenzimidazole-2-carbamate and 1.94 g of 4-fluorobenzenesulfonyl chloride at about 10° C. The mixture is then stirred at room temperature for 2 h, 100 ml of 2N acetic acid are added while cooling, and the resulting precipitate is filtered off with suction, washed with water and dried. Melting point 236° C., decomposition, from dimethylformamide/methanol.

Workup

  1. temperaturewhile cooling
  2. filtrationthe resulting precipitate is filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d0b27162300f42dea1d082bb33dc2d64
Source dataset
uspto-grants-1987_01
Patent number
US04639463

Reaction notes

Loading…