Wy 13876 → Tilomisole

HRID 358327Notes

Reaction equation

HRID 358327 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[N:15]3[C:11](=[N:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=43)[S:10][CH:9]2[CH2:20][C:21]([OH:23])=[O:22])=[CH:4][CH:3]=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11](=[N:12][C:13]4[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=43)[S:10][C:9]=2[CH2:20][C:21]([OH:23])=[O:22])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 162367Wy 13876

Product 1

HCID 42747Tilomisole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(p-Chlorophenyl)-2,3-dihydro-3-hydroxy-thiazolo[3,2-a]-benzimidazole-2-acetic acid, (5.0 g.) is suspended in a solution of 100 ml. of a 6N NCl and 200 ml. of dioxane. The mixture is heated at reflux for 18 hours. The solution is concentrated in vacuo to 50 ml. To the concentrate is added 200 ml. of water, and sufficient 4N NaOH solution to dissolve all the solids. The alkaline solution is made acidic with acetic acid. The solid is collected, washed well with water and airdried. The crude material is recrystallized from dimethoxyethane. The product (2.0 g.) melts at 242°-243° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe solution is concentrated in vacuo to 50 ml
  4. additionTo the concentrate is added 200 ml
  5. dissolutionof water, and sufficient 4N NaOH solution to dissolve all the solids
  6. customThe solid is collected
  7. washwashed well with water
  8. customThe crude material is recrystallized from dimethoxyethane

Sources & evidence

ORD record
ord-e62821b0b8174bfe8d79592bb4038426
Source dataset
uspto-grants-1984_08
Patent number
US04466957

Reaction notes

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