Methanol → Methyl 3-(1H-Imidazol-5-Yl)Propanoate

HRID 870606Notes

Reaction equation

HRID 870606 reaction equation
S(Cl)(Cl)=O.[NH:5]1[C:9]([CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:8][N:7]=[CH:6]1.[CH3:15]O>>[NH:5]1[C:9]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:7]=[CH:6]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 706301H-Imidazole-5-propanoic acid

Product 1

HCID 565491Methyl 3-(1H-Imidazol-5-Yl)PropanoateYield 100%

Procedure

Add thionyl chloride (0.75 mL) to a −78° C. solution of 3-(1H-imidazol-5-yl)propanoic acid (2.0 g; 1.0 equiv; 14.27 mmoles) in methanol (18 mL). Allow the reaction mixture to warm to ambient temperature and stir for 30 minutes. Add saturated sodium bicarbonate (10 mL) to the reaction mixture and concentrate. Suspended the resulting residue in methanol (10 mL) and filter, then concentrate to afford methyl 3-(1H-imidazol-5-yl)propanoate (2.2 g; 100%) as a white solid: MS (m/z): 155(M+1).

Workup

  1. concentrationAdd saturated sodium bicarbonate (10 mL) to the reaction mixture and concentrate
  2. filtrationfilter
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-ccf8d6c040c248cea7fba67c38a2a160
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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