3-Mercaptopropionic Acid → 2-(2,4-dichlorophenyl)-3-(2-carboxyethylthio)-1-(1H-1,2,4-triazol-1-yl)-propan-2-ol
Reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[H-].[Na+].S(O)(=O)(=O)C.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]1([CH2:25][N:26]2[CH:30]=[N:29][CH:28]=[N:27]2)[CH2:24][O:23]1>CN(C)C=O>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]([OH:23])([CH2:24][S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])[CH2:25][N:26]1[CH:30]=[N:29][CH:28]=[N:27]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
3-Mercaptopropionic acid (1.2 g, 1.1 equiv.) was dissolved in dimethylformamide (50 ml) and cooled to 5° C. in an ice bath. Sodium hydride (1.6 g of a 50% dispersion in oil, 3.3 equiv.) was added in portions over 10 minutes, followed by 2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane mesylate (3.6 g). After stirring overnight (19 hours) the mixture was poured onto ice (200 ml) and extracted with methylene chloride (3×50 ml). The aqueous layer was adjusted to pH3 with hydrochloric acid (5N) and extracted with methylene chloride (3×50 ml). The organic extracts were combined, washed with saturated sodium chloride solution (2×50 ml), dried (Na2SO4), and evaporated under reduced pressure to a gum, 5.6 g.
Workup
- additionwas poured onto ice (200 ml)
- extractionextracted with methylene chloride (3×50 ml)
- extractionextracted with methylene chloride (3×50 ml)
- washwashed with saturated sodium chloride solution (2×50 ml)
- dry with materialdried (Na2SO4)
- customevaporated under reduced pressure to a gum, 5.6 g
Sources & evidence
- ORD record
- ord-2895e65b48b7434e840302d5a192cbab
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04585778
Reaction notes
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