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

HRID 50207Notes

Reaction equation

HRID 50207 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-methoxymethylbenzothiazole-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 while 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. temperaturewhile being cooled with ice
  4. customThe pinkish-beige compound thereby precipitated
  5. filtrationfiltered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-e70aab72bf2147f0ada00b3d85323164
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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