Lithium Hydroxide → 2-(Methylsulfanyl)-1,3-thiazole-4-carboxylic acid

HRID 1948298Notes

Reaction equation

HRID 1948298 reaction equation
[CH3:1][S:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10]CC)=[O:9])[N:7]=1.[Li+].[OH-]>CO>[CH3:1][S:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([OH:10])=[O:9])[N:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 25219524ethyl 2-(methylthio)-1,3-thiazole-4-carboxylate

Product 1

HCID 252195252-(Methylsulfanyl)-1,3-thiazole-4-carboxylic acidYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-(methylthio)-1,3-thiazole-4-carboxylate (5.0 g) (Sinha, Subhash C et al. Tet. Lett. 2000, 41 (43), 8243-8246) was dissolved in MeOH (50 ml) and 2N LiOH (74 ml) was added. After stirring at room temperature for five minutes the reaction mixture was concentrated to remove MeOH and the residue was suspended in water and acidified with conc. HCl to pH 3. The white precipitate was filtered and dried to yield the title compound (3.42 g). NMR: 2.72 (s, 3H), 8.35 (s, 1H).

Workup

  1. concentrationwas concentrated
  2. customto remove MeOH
  3. filtrationThe white precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-abe20f0ba6814356a18da7db16d140e8
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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