Lithium hydroxide, monohydrate → 4-(4-Nitrophenyl)thiazole-2-carboxylic acid

HRID 1024432Notes

Reaction equation

HRID 1024432 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]([O:17]CC)=[O:16])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].O.[OH-].[Li+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([C:15]([OH:17])=[O:16])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10084925Ethyl 4-(4-nitrophenyl)-1,3-thiazole-2-carboxylate2×

Product 1

HCID 152742424-(4-Nitrophenyl)thiazole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 4-(4-nitrophenyl)thiazole-2-carboxylate (Intermediate 3, step A, 7.0 g) in THF (70 ml) was added (1 ml) 1N lithium hydroxide monohydrate solution and reaction mixture was stirred for 4 hours at RT. Organic solvent was concentrated, water was added, and the reaction mixture was made acidic by dilute HCl solution. This resulted in precipitation of white solid, which was filtered and washed with water. The solid was dried to obtain the title compound. Yield: 6.2 gm (98%). 1H NMR (DMSO-d6, 300 MHz): δ 8.78 (s, 1H), 8.32 (d, 4H).

Workup

  1. concentrationOrganic solvent was concentrated
  2. additionwater was added
  3. customThis resulted in precipitation of white solid, which
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe solid was dried

Sources & evidence

ORD record
ord-8f44e5169d0446bbb6ea100d619b50be
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

Loading…