2-(Methylthio)benzoxazole → 2-(1,3-Benzoxazol-2-ylamino)ethanol
Reaction equation
CS[C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1>C(CN)O>[O:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[NH:7][CH2:6][CH2:5][OH:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To 2-methylsulfanyl-benzooxazole [compound of Step I] (25 g, 150 mmol), ethanolamine (253 g, 250 mL) was added and the reaction mixture was heated at 100° C. for 1.5 hours. The reaction mixture was poured on crushed ice-water mixture and extracted with ethyl acetate (3×1 L). The ethyl acetate layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated to give 2-(benzooxazol-2-ylamino)-ethanol.
Workup
- additionThe reaction mixture was poured
- extractionextracted with ethyl acetate (3×1 L)
- washThe ethyl acetate layer was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-61ee4b4edff64bf48a693e0bad2f7f33
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263587B2
Reaction notes
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