Hydrochloric Acid → N-(1-hydroxy-2-methylpropan-2-yl)acetamide

HRID 1158416Notes

Reaction equation

HRID 1158416 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[CH3:7][C:8](OC(C)=O)=[O:9].C([O-])(O)=O.[Na+].Cl>O>[OH:4][CH2:3][C:2]([NH:1][C:8](=[O:9])[CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 118072-Amino-2-methyl-1-propanolHCID 516892Sodium Bicarbonate

Product 1

HCID 519166N-(1-hydroxy-2-methylpropan-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-2-methyl-propan-1-ol (2.0 mL, 20.4 mmol), acetanhydride (1.9 mL, 20.4 mmol) and NaHCO3 (2.6 g, 30.6 mmol) in H2O (20 mL) is stirred at RT for 16 h. For workup 1N HCl is added and the mixture is extracted with ethyl acetate. Drying (Na2SO4) of the combined extracts, filtration and evaporation of the solvent yields the title compound as a colorless solid. MS (LC-MS): [M+H]+=132.2. tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 0.38 min.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. customDrying
  3. filtration(Na2SO4) of the combined extracts, filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-5c240cb6dee54cdf94e9a46e22cf6fa3
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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