2-Amino-2-methyl-1-propanol → 4-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide
Reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]([C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl>[C:7]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[O:16])=[CH:18][CH:19]=1)([CH3:10])([CH3:8])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
30.95 g (347 mmol) of 2-amino-2-methyl-1-propanol was weighed into a 500 mL Erlenmeyer flask fitted with a stir bar and septum. Added 200 mL CH2Cl2. Established and maintained nitrogen atmosphere. Stirred the solution in an ice/water bath. Added 34 mL (174 mmol) of 4-tert-butylbenzoyl chloride dropwise over 30 min. A white precipitate formed. Stirred at room temperature overnight. Removed the solids by filtration and washed with CH2Cl2. Removed the solvent from the filtrate on rotavap and dried at 60°/4 torr to obtain 45.79 g of the title compound as a light yellow resin. MS (ESI) 248 (M−H)31 .