Ethyl 2-(4-nitrophenyl)thiazole-4-carboxylate → 2-(4-nitrophenyl)-1,3-thiazole-4-carboxylic Acid

HRID 75855Notes

Reaction equation

HRID 75855 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[C:13]([C:15]([O:17]CC)=[O:16])[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]>C1COCC1.[Li+].[OH-]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][CH:12]=[C:13]([C:15]([OH:17])=[O:16])[N:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 1

HCID 3742475Ethyl 2-(4-nitrophenyl)thiazole-4-carboxylate

Product 1

HCID 14738252-(4-nitrophenyl)-1,3-thiazole-4-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of Ethyl 2-(4-nitrophenyl)thiazole-4-carboxylate in THF, 1N LiOH was added at RT and stirred for 2-3 hr. After completion of reaction THF was removed under reduced pressure. Obtained material was dissolved in water acidified with 1N HCl and white solid precipitated out. It was filtered and dried. Yield 4.4 gm (97%). MS (ESI) m/z: 249(M−H)−; 1HNMR (DMSO-d6, 300 MHz): δ 13.233 (s, 1H), 8.658 (s, 1H), 8.358 (d, 2H), 8.269 (d, 2H).

Workup

  1. customwas removed under reduced pressure
  2. dissolutionObtained material was dissolved in water
  3. customprecipitated out
  4. filtrationIt was filtered
  5. customdried

Sources & evidence

ORD record
ord-ff04c9b2d93c40fcb896bd73e490164e
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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