Sulfuric Acid → HCID 67496730, compound

HRID 2365239Notes

Reaction equation

HRID 2365239 reaction equation
O[CH:2]([C:13]1[N:14]([CH3:24])[N:15]=[N:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH2:3][C:4]1[S:5][C:6]([C:10]([OH:12])=[O:11])=[C:7]([CH3:9])[N:8]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:9][C:7]1[N:8]=[C:4](/[CH:3]=[CH:2]/[C:13]2[N:14]([CH3:24])[N:15]=[N:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[S:5][C:6]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67495517HCID 67495517, compound

Product 1

HCID 67496730HCID 67496730, compoundYield 79.1%

Conditions

Temperature
160 °C

Procedure

A suspension of 2-[2-hydroxy-2-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-ethyl]-4-methyl-thiazole-5-carboxylic acid (152 mg, 0.44 mmol) in sulfuric acid (conc., 2.59 mL, 48.4 mmol) was heated at 160° C. under Ar for 7 h. After cooling to room temperature the mixture was poured into ice, adjusted to pH 4 with NaOH (6 N) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (114 mg, 79%) as an a yellow solid after trituration from methanol-water. MS: m/e=326.2 [M−H]−.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. additionwas poured into ice
  3. extractionextracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-fbb5aac0d6784690b588cb736945ca9f
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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