Hydrochloric Acid → 5-(4-Nitrophenyl)thiazole-2-carboxylic acid

HRID 1024429Notes

Reaction equation

HRID 1024429 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]([C:15]([O:17]CC)=[O:16])=[N:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].Cl>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[N:12][CH:11]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53404682Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate2×

Product 1

HCID 671503095-(4-Nitrophenyl)thiazole-2-carboxylic acidYield 76.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(4-nitrophenyl)thiazole-2-carboxylate (Intermediate 2, step A, 3.6 g) was dissolved in THF (90 ml). 1 Molar aqueous NaOH (52 ml) was added and stirred at RT for 15-20 minutes. The reaction mixture was acidified with 1M HCl, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to get pale yellow colored solid. Solid was crystallized in EtOAc/Pet ether to yield 2.48 g (76%) of the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 14.21 (bs, 1H), 8.7 (s, 1H), 8.31 (d, 2H), 8.1 (d, 2H); MS (ES+): m/z 251 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get pale yellow colored solid
  6. customSolid was crystallized in EtOAc/Pet ether

Sources & evidence

ORD record
ord-d63e61d66f8f4924865d6cea9ab620ae
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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