Ethanolamine → 4-Hydroxy-3-methoxy-N,N-di(propan-2-yl)benzamide
Reaction equation
C([O:4][C:5]1[CH:19]=[CH:18][C:8]([C:9]([N:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])=[O:10])=[CH:7][C:6]=1[O:20][CH3:21])(=O)C.NCCO>>[OH:4][C:5]1[CH:19]=[CH:18][C:8]([C:9]([N:11]([CH:12]([CH3:13])[CH3:14])[CH:15]([CH3:17])[CH3:16])=[O:10])=[CH:7][C:6]=1[O:20][CH3:21]Participants
Procedure
The combined filtrate (about 1260 mL), containing 4-acetoxy-3-methoxy-N,N-bis(1-methylethyl)-benzamide, is treated at room temperature under nitrogen while stirring with 2-aminoethanol (43.1 g, 42.6 mL) added dropwise over a 5 minute period. The reaction mixture is then heated at 78°-85° for 5 hours. The heat source is removed and water (400 mL) is added slowly over a period of 30 minutes. The stirred slurry is cooled to room temperature and stirring at room temperature is continued for 16 hours. The suspension is cooled to 5° C. and filtered. The resulting solid is washed with xylenes and dried in a vacuum oven at 40°-45° C. for 48 hours to obtain 4-hydroxy-3-methoxy-N,N-bis(1-methylethyl)benzamide; 1H-NMR (CDCl3): δ1.10-1.50 (m, 12H), 3.62-3.80 (m, 2H), 3.82 (s, 3H), 6.42-6.70 (m, 1H), 6.72-6.88 (m, 3H).
Workup
- additionis treated at room temperature under nitrogen
- additionadded dropwise over a 5 minute period
- temperatureThe reaction mixture is then heated at 78°-85° for 5 hours
- customThe heat source is removed
- additionwater (400 mL) is added slowly over a period of 30 minutes
- temperatureThe suspension is cooled to 5° C.
- filtrationfiltered
- washThe resulting solid is washed with xylenes
- customdried in a vacuum oven at 40°-45° C. for 48 hours
Sources & evidence
- ORD record
- ord-e45ddc5020cd463186e910035c1a47cf
- Source dataset
- uspto-grants-1995_09
- Patent number
- US05451700
Reaction notes
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