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

HRID 1773452Notes

Reaction equation

HRID 1773452 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-25070e03d5084c329b73469b2157ec2a
Source dataset
uspto-grants-2016_02
Patent number
US09255085B2

Reaction notes

Loading…