Hydrochloric Acid → 6-Hydroxy-1,3-benzothiazole-2-carboxylic acid

HRID 1626336Notes

Reaction equation

HRID 1626336 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([C:9]([O:11]C)=[O:10])[S:8][C:4]=2[CH:3]=1.[OH-].[Na+].Cl>>[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([C:9]([OH:11])=[O:10])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15106734Methyl 6-hydroxybenzothiazole-2-carboxylate

Product 1

HCID 154983676-Hydroxy-1,3-benzothiazole-2-carboxylic acidYield 102.5%

Procedure

A mixture of methyl 6-hydroxybenzo[d]thiazole-2-carboxylate (0.21 g, 1 mmol) and 1N aqueous sodium hydroxide (2 mL) was stirred at room temperature overnight. The reaction mixture was then carefully acidified with concentrated hydrochloric acid. The precipitate formed was filtered, washed with water, and dried under reduced pressure to afford 6-hydroxybenzo[d]thiazole-2-carboxylic acid as a white solid (0.20 g, 99%). 1H-NMR (DMSO-d6, 300 MHz): δ 10.20 (s, 1H), 7.96 (m, 1H), 7.44 (m, 1H), 7.06 (m, 1H) ppm; MS (ESI): 196.1 (M+1).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-653d575b5a4743548a2046a783e66293
Source dataset
uspto-grants-2014_07
Patent number
US08785449B2

Reaction notes

Loading…