Sulfuric Acid → 3-[5-(2-Amino-4-pyridyl)-2-ethyl-1,3-thiazol-4-YL]benzoic acid

HRID 1727372Notes

Reaction equation

HRID 1727372 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#N)[CH:16]=2)[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)[OH:24].[OH-:28].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][C:11]([CH2:13][CH3:14])=[N:10][C:9]=2[C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[C:21]([OH:24])=[O:28])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 229327263-[5-(2-Aminopyridin-4-yl)-2-ethyl-1,3-thiazol-4-yl]benzonitrile

Product 1

HCID 534254603-[5-(2-Amino-4-pyridyl)-2-ethyl-1,3-thiazol-4-YL]benzoic acidYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-(2-amino-4-pyridyl)-4-(3-cyanophenyl)-2-ethyl-1,3-thiazole (0,50 g, 1.6 mmol) in acetic acid (5 mL) was added 50% sulfuric acid (2.0 mL), and the mixture was stirred for 6 hours at 110° C. The reaction mixture was basified with aqueous sodium hydroxide solution and washed with ethylacetate. The aqueous phase was neutralized with hydrochloric acid, and the deposited crystal was washed with water and ethyl ether to obtain a title compound (0.45 g, yield 84%).

Workup

  1. washwashed with ethylacetate
  2. washthe deposited crystal was washed with water and ethyl ether

Sources & evidence

ORD record
ord-8b7c3f3e211c4ab2b7656758f6d2b39b
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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