Triethylamine → 4-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide

HRID 251436Notes

Reaction equation

HRID 251436 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[NH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34]>ClCCl>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[O:21])=[CH:22][CH:23]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acid

Product 1

HCID 141804474-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamideYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (6.6 ml, 76 mmol, 1.2 eq) is added into a cold (ice bath) solution of 4-benzyloxy-benzoic acid (14.38 g, 63 mmol, 1 eq) and triethylamine (43.8 ml, 315 mmol, 5 eq) in dichloromethane (400 ml). The dark red mixture is warmed to room temperature and stirred for 2 h and then cooled to 0° C. A solution of 2-amino-2-methyl-propan-1-ol (5.6 g, 63 mmol, 1 eq) in dichloromethane (20 ml) is added and the mixture is stirred overnight at room temperature. The solvent is then removed under vacuum and the residue is dissolved in dichloromethane. This solution is washed once with water and the aqueous layer is extracted with dichloromethane. The organic layers are washed with a solution of 0.1 M sodium hydroxide and dried over magnesium sulfate. The solvent is removed under vacuum, to afford 15 g of 4-(benzyloxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide ax1 as a brown solid.

Workup

  1. temperaturecooled to 0° C
  2. stirringthe mixture is stirred overnight at room temperature
  3. customThe solvent is then removed under vacuum
  4. dissolutionthe residue is dissolved in dichloromethane
  5. washThis solution is washed once with water
  6. extractionthe aqueous layer is extracted with dichloromethane
  7. washThe organic layers are washed with a solution of 0.1 M sodium hydroxide
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is removed under vacuum

Sources & evidence

ORD record
ord-9863f958e00047f5a0fff65a2349f888
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

Loading…