3-Bromopropionic acid → 3-(1,3-benzoxazol-2-ylsulfanyl)propanoic acid

HRID 2416940Notes

Reaction equation

HRID 2416940 reaction equation
Br[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[SH:7][C:8]1[O:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1.[OH-].[K+]>C(O)C>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[S:7][CH2:2][CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 115533-Bromopropionic acidHCID 14797Potassium HydroxideHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 7397763-(1,3-benzoxazol-2-ylsulfanyl)propanoic acidYield 58.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (EtOH) (35 ml), 3-bromopropanoic acid (1.53 g, 10 mmols) and 2-mercaptobenzoxazole (1.51 g, 10mmols) were added in that order to an aqueous (15 ml) solution of potassium hydroxide (KOH) (1.0 g, 17.8 mmols), and heated under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, water was added to the resulting residue, and this was made acidic (pH=1) with 1N HCl added thereto. The precipitate formed was taken out through filtration, and crystallized in acetone-ether-hexane to obtain 1.3 g (58%) of 3-(benzoxazol-2-ylthio)propanoic acid as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added to the resulting residue
  5. additionadded
  6. customThe precipitate formed
  7. filtrationwas taken out through filtration
  8. customcrystallized in acetone-ether-hexane

Sources & evidence

ORD record
ord-356bb8372b754fb38895009b9f4c9883
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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