2-Amino-2-methyl-1-propanol → Benzoyl chloride, 3,4,5-trimethoxy-

HRID 376013Notes

Reaction equation

HRID 376013 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:8])=[O:7].[NH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19].S(Cl)(Cl)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:15][O:14][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:11]=1[O:12][CH3:13])[C:6]([Cl:8])=[O:7].[CH3:20][C:17]1([CH3:21])[CH2:18][O:19][C:6]([C:5]2[CH:9]=[C:10]([O:14][CH3:15])[C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:16]1

Participants

7

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-2×

Product 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 158174664,4-Dimethyl-2-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 16.2 g (70 mmoles) of 3,4,5-trimethoxybenzoyl chloride (compound 1) in 40 ml of dry methylene chloride was added dropwise to a solution of 12.5 g (140 mmoles) of 2-amino-2-methyl-1-propanol in 50 ml of dry methylene chloride under cooling in an ice-bath for 30 minutes. After completion of the addition, the mixture was stirred for additional 45 minutes and the reaction solution was filtered through a glass filter. The filtered cake was washed with methylene chloride and the filtrate was combined with the washing, which was followed by concentration in vacuo. The residue was dissolved in 30 ml of dry toluene, and 6.64 ml (91.0 mmoles) of thionyl chloride was added dropwise thereto under cooling in an ice-bath. The mixture was allowed to warm to room temperature, while being stirred for additional 45 minutes. Subsequently, 20 g of ice and aqueous sodium hydroxide (18 g of NaOH in 60 ml of water) were added to the mixture and then the mixture was extracted with toluene. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. After concentration in vacuo, the residue was crystallized from 70 ml of n-hexane to give 16.8 g (90.6% from compound 1) of the desired compound. Melting point: 87°-89° C.

Workup

  1. temperatureunder cooling in an ice-bath for 30 minutes
  2. additionAfter completion of the addition
  3. filtrationthe reaction solution was filtered through a glass
  4. filtrationfilter
  5. washThe filtered cake was washed with methylene chloride
  6. concentrationwas followed by concentration in vacuo
  7. dissolutionThe residue was dissolved in 30 ml of dry toluene
  8. temperatureunder cooling in an ice-bath
  9. stirringwhile being stirred for additional 45 minutes
  10. extractionthe mixture was extracted with toluene
  11. washThe extract was washed with water and brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationAfter concentration in vacuo
  14. customthe residue was crystallized from 70 ml of n-hexane

Sources & evidence

ORD record
ord-3584acf54ad14c7699f12102f9659683
Source dataset
uspto-grants-1996_01
Patent number
US05488134

Reaction notes

Loading…