2-Amino-2-methyl-1-propanol → 4-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide

HRID 1644206Notes

Reaction equation

HRID 1644206 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

HCID 118072-Amino-2-methyl-1-propanolHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 3200764-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamideYield 105.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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)−.

Workup

  1. customfitted with a stir bar
  2. temperatureEstablished and maintained nitrogen atmosphere
  3. customA white precipitate formed
  4. stirringStirred at room temperature overnight
  5. customRemoved the solids
  6. filtrationby filtration
  7. washwashed with CH2Cl2
  8. customRemoved the solvent from the filtrate on rotavap
  9. customdried at 60°/4 torr

Sources & evidence

ORD record
ord-4fe8c10b03ac4766bb53979444cb6a2f
Source dataset
uspto-grants-2012_02
Patent number
US08124604B2

Reaction notes

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