Water → HCID 86610488, compound

HRID 2416185Notes

Reaction equation

HRID 2416185 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[NH:9][CH:8]=[CH:7][S:6]1.O>CO>[N:13]1[CH:12]=[CH:11][C:10]([C:5]2([CH2:4][C:3]([OH:16])=[O:2])[NH:9][CH:8]=[CH:7][S:6]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 962WaterHCID 86610487HCID 86610487, compound

Product 1

HCID 86610488HCID 86610488, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

In a 100-mL, round-bottomed flask was placed 2-(4-pyridyl)-thiazole acetic acid methyl ester (Step a, 818 mg, 3.5 mmol), LiOH monohydrate (154 mg, 3.67 mmol) in MeOH (20 mL), and H2O (2 mL). The solution was heated to 75° C. for 2 h, cooled to RT, and concentrated. The resulting yellow solid was dissolved in H2O (10 mL) and extracted with EtOAc (15 mL). The aqueous layer was acidified with 1N aqueous HCl (3.67 mL). The resulting precipitate was filtered, and washed with H2O (10 mL) to afford 2-(4-pyridyl)-thiazole acetic acid as a light yellow solid. Mp: >240° C. MS m/z: 221 (M+1). Calc'd for C10H8N2O2S: 220.03.

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. dissolutionThe resulting yellow solid was dissolved in H2O (10 mL)
  4. extractionextracted with EtOAc (15 mL)
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with H2O (10 mL)

Sources & evidence

ORD record
ord-bc81da885dba4f36b76da4bc5ac106f8
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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