5-(Bromoacetyl)-2-hydroxybenzoic acid → HCID 53642025, compound

HRID 1414523Notes

Reaction equation

HRID 1414523 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12]Br)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15]([NH2:18])(=[S:17])[CH3:16]>C(O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:18]=[C:15]([CH3:16])[S:17][CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 2554785-(Bromoacetyl)-2-hydroxybenzoic acidHCID 2723949Thioacetamide

Product 1

HCID 53642025HCID 53642025, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 53 g (0.2 mol) of 2-hydroxy-5-(α-bromoacetyl) benzoic acid in 250 ml of slightly warm ethanol was dropped, for 15 minutes, in a solution of 15 g (0.2 mol) of thioacetamide in 60 ml of ethanol, while stirring vigorously. The reaction was slightly exothermic, and a white product gradually precipitated. Stirring was maintained for one hour, then the reaction mixture was diluted with 500 ml of water. The precipitate was filtered off, washed with water and the product was recrystallized from ethanol. 40.6 g of 2-hydroxy 5-(2-methyl thiazol-4-yl) benzoic acid, M.P. (K.B.) 250°-253° C, were obtained (yield 83%). A second yield of product was obtained by concentration of the ethanolic mother liquors. 3.1 g (0.0425 mol) of diethylamine was added to a suspension of 10 g (0.0425 mol) of the acid prepared above in 50 ml of ethanol. The mixture was stirred for 30 minutes then concentrated to dryness. The residue was recrystallized from benzene. 10.3 g of diethylammonium 2-hydroxy-5-(2-methyl thiazol-4-yl) benzoate are obtained, M.P. (M.K.) 128°-132° C with progressive recrystallization and second M.P. 249°-250° C (yield 78 %).

Workup

  1. customa white product gradually precipitated
  2. stirringStirring
  3. temperaturewas maintained for one hour
  4. additionthe reaction mixture was diluted with 500 ml of water
  5. filtrationThe precipitate was filtered off
  6. washwashed with water
  7. customthe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-76b1f56f42654541bb1adcdeb17ef255
Source dataset
uspto-grants-1977_01
Patent number
US04001420

Reaction notes

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