Hydrochloric Acid → 2-(2-Hydroxyphenyl)-4-thiazoleacetic Acid

HRID 260031Notes

Reaction equation

HRID 260031 reaction equation
C([O:3][C:4](=[O:18])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[OH:17])[S:9][CH:10]=1)C.[Li+].[OH-].Cl.[Na+].[Cl-]>C1COCC1.CCOC(C)=O.CO>[OH:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:18])=[O:3])[N:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 5234Sodium ChlorideHCID 1360263402-(2-Hydroxyphenyl)-4-thiazoleacetic Acid Ethyl Ester

Product 1

HCID 1357374432-(2-Hydroxyphenyl)-4-thiazoleacetic AcidYield 99.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 4a (824 mg, 3.13 mmol) in THF (5 mL)/MeOH (5 mL) was treated with 2N LiOH (4 mL), the resultant mixture was stirred at ambient temperature under nitrogen for 30 min. The mixture was treated with 5N HCl (2 mL), followed by adding EtOAc (50 mL) and solid NaCl to saturate the aq. layer. The organic layer was separated, washed with brine (20 mL×2), dried over MgSO4, filtered, and concentrated in vacuo to give a solid residue. After recrystallization from acetone/hexane, 5a (730 mg, 99%) was obtained as a white solid. mp 173.0°-174.0° C.; IR (KBr) 3250-2400 (br), 3108, 1696, 1223 cm-1 ; 1H NMR (DMSO-d6) δ3.76 (2H, s, CH2), 6.89 (1H, t, J=7.8 Hz, Ar), 6.96 (1H, d, J=7.8 Hz, Ar), 7.26 (1H, t, J=7.8 Hz, Ar), 7.45 (1H, s), 7.92 (1H, d, J=7.8 Hz, Ar), 11.33 (1H, s, OH), 12.42 (1H, br s, CO2H); FABMS m/z 235 (M+), 236 (M+ +1); Anal. Calcd for C11H9NO3S: C, 56.16; H, 3.86; N, 5.95. Found: C, 56.30; H, 3.85; N, 6.10.

Workup

  1. concentrationto saturate the aq. layer
  2. customThe organic layer was separated
  3. washwashed with brine (20 mL×2)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a solid residue
  8. customAfter recrystallization from acetone/hexane

Sources & evidence

ORD record
ord-2194519ab50540deb5668ab6cf7dd9e7
Source dataset
uspto-grants-1996_06
Patent number
US05525599

Reaction notes

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