Sodium Hydroxide → 2-(Methoxymethyl)-1,3-benzothiazole-5-carboxylic acid

HRID 2288338Notes

Reaction equation

HRID 2288338 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]([O:15]CC)=[O:14])=[CH:9][C:7]=2[N:8]=1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18412295HCID 18412295, compound

Product 1

HCID 184125372-(Methoxymethyl)-1,3-benzothiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.1 g (8.36 mMol) of ethyl 2-methoxymethyl-benzothiazole-5-carboxylate and 16 ml of 2N sodium hydroxide solution was stirred into 60 ml ethanol for 1 hour at room temperature. Then the alcohol was distilled off, the crude product was taken up in 20 ml water, washed with 50 ml diethylether and the aqueous phase was acidified with concentrated hydrochloric acid whilst being cooled with ice. The pinkish-beige compound thereby precipitated was suction filtered, washed with water and dried. Yield: 1.6 g (86% of theory), Rf value: 0.12 (silica gel; dichloromethane/ethanol=29:1)

Workup

  1. distillationThen the alcohol was distilled off
  2. washwashed with 50 ml diethylether
  3. temperaturewhilst being cooled with ice
  4. customThe pinkish-beige compound thereby precipitated
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f181465576ba4c94a2b641cfe0dd7398
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

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