Water → 1-[3-(2-Hydroxyethyl)phenyl]-2-imidazolidinone
Reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:8]=[C:9]([CH2:13][C:14](OC)=[O:15])[CH:10]=[CH:11][CH:12]=1.[BH4-].[Li+].O>ClCCl>[OH:15][CH2:14][CH2:13][C:9]1[CH:8]=[C:7]([N:3]2[CH2:4][CH2:5][NH:6][C:2]2=[O:1])[CH:12]=[CH:11][CH:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
Methyl [3-(2-oxo-1-imidazolidinyl)phenyl]acetate was dissolved in dry dichloromethane (10 vol). Lithium borohydride (2M solution in THF, 4.3 vol) was added dropwise over 1 hour at 20° C. The resulting suspension was stirred at 20° C. for 2.5 hours. Water (2 vol) is added dropwise at 20° C. over 60 minutes. The resulting suspension was concentrated to 2 vol and aqueous ammonium chloride solution (7%, acidity corrected with 10% hydrochloric acid to pH 3, 3 vol) was added. The suspension was stirred at 20° C. for 2 hours then filtered. The filter-cake was washed thoroughly with aqueous ammonium chloride solution (7%, acidity corrected with 10% hydrochloric acid to pH 3, 2 vol) and water (2 vol) until the filtrate had an acidity of pH 7. The filter-cake was dried at 80° C. to give the title compound (75% th.).
Workup
- concentrationThe resulting suspension was concentrated to 2 vol and aqueous ammonium chloride solution (7%, acidity corrected with 10% hydrochloric acid to pH 3, 3 vol)
- additionwas added
- stirringThe suspension was stirred at 20° C. for 2 hours
- filtrationthen filtered
- washThe filter-cake was washed thoroughly with aqueous ammonium chloride solution (7%, acidity corrected with 10% hydrochloric acid to pH 3, 2 vol) and water (2 vol) until the filtrate
- customThe filter-cake was dried at 80° C.
Sources & evidence
- ORD record
- ord-856230cdf20e4f1da59e014b68185ad5
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07279481B2
Reaction notes
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