Wy 13876 → Tilomisole

HRID 2199054Notes

Reaction equation

HRID 2199054 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 6 N 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 4 N 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 air-dried. 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 4 N NaOH solution to dissolve all the solids
  6. customThe solid is collected
  7. washwashed well with water
  8. customair-dried
  9. customThe crude material is recrystallized from dimethoxyethane

Sources & evidence

ORD record
ord-c17592457d414d92a2f2c56cc3e6bcb9
Source dataset
uspto-grants-1982_11
Patent number
US04361574

Reaction notes

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