Lithium Hydroxide → 2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carboxylic acid

HRID 901961Notes

Reaction equation

HRID 901961 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:13][C:14]2[S:15][CH:16]=[C:17]([C:19]([O:21]CC)=[O:20])[N:18]=2)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:13][C:14]2[S:15][CH:16]=[C:17]([C:19]([OH:21])=[O:20])[N:18]=2)[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69206070HCID 69206070, compound

Product 1

HCID 692074192-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carboxylate (2.19, 5.2 mmol) was added to mixture of 1N lithium hydroxide solution (10 ml, 10 mmol) and dioxan (20 ml) and heated to 50° C. until a solution was obtained. The mixture was stirred at room temperature for a further 3 days. The mixture was evaporated, taken up in EtOAc and acidified with 1N potassium hydrogen sulphate solution. The phases were separated and the organic phase washed with water and brine, dried and reduced to afford 2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carboxylic acid (1.86 g, 95%) as a white solid.

Workup

  1. customwas obtained
  2. customThe mixture was evaporated
  3. customThe phases were separated
  4. washthe organic phase washed with water and brine
  5. customdried

Sources & evidence

ORD record
ord-adcc4646ff894c33bd5e5edf168701bd
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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