Sodium Hydroxide → HCID 59457499, compound

HRID 1710798Notes

Reaction equation

HRID 1710798 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([O-:20])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][C:14]([C:18]([OH:20])=[O:19])=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86624422HCID 86624422, compound

Product 1

HCID 59457499HCID 59457499, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i105 (14.1 mmol, 1 eq, 4.6 g) and 2 M sodium hydroxide (28.2 mmol, 2 eq, 14.1 ml) in methanol (100 ml) is stirred at 70° C. overnight. The mixture is concentrated to dryness and taken up in a minimum of water. The aqueous phase is acidified by 1 N hydrogen chloride to reach pH 2 and poured into ice to afford precipitation of a white solid. The solid is filtered and dried under reduced pressure to give 3.9 g of 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid i106 as a white solid. This solid is used as such in the next step.

Workup

  1. concentrationThe mixture is concentrated to dryness
  2. additionpoured into ice
  3. customto afford
  4. customprecipitation of a white solid
  5. filtrationThe solid is filtered
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5a05977c1364ee99a110d2eeb23d155
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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