2-Aminopropanol → 2,2'-(1,3-Phenylene)bis(4-methyl-4,5-dihydro-1,3-oxazole)

HRID 263655

Reaction equation

HRID 263655 reaction equation
[C:1]([OH:12])(=O)[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=O)[CH:3]=1.[NH2:13][CH:14]([CH3:17])[CH2:15]O>>[CH3:15][CH:14]1[CH2:17][O:7][C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([C:1]3[O:12][CH2:15][CH:14]([CH3:17])[N:13]=3)[CH:3]=2)=[N:13]1

Participants

3

Reactant 2

HCID 51262-AminopropanolHCID 8496Isophthalic Acid

Product 1

HCID 159032242,2'-(1,3-Phenylene)bis(4-methyl-4,5-dihydro-1,3-oxazole)

Conditions

Temperature
174 fahrenheit

Procedure

50 g of isophthalic acid is refluxed at 165° C. (329° F.) for 18 hr in 150 mL of 2-amino-1-propanol. The bulk of the excess amino alcohol is then distilled off and the remaining viscous liquid dissolved in 200 mL of 2% NaOH. The resulting bis-N-(1-methyl-2-hydroxyethyl)isophthalamide is then precipitated in acetone, filtered and dried. To 10 g of the aforementioned diamide is slowly added 300 mL of thionyl chloride with stirring. The mixture is then heated to reflux (79° C., 174° F.) for approximately 1 hour, after which time the homogenous yellow solution is cooled and poured into diethylether to precipitate the 4,4'-dimethyl-2,2'-(1,3-phenylene)bis(oxazoline) hydrochloride salt. The salt is neutralized using 20% NaOH and the free base extracted into ether. The organic phase is then dried and evaporated to give 4,4'-dimethyl-2,2'-(1,3-phenylene)bis(oxazoline).

Workup

  1. distillationThe bulk of the excess amino alcohol is then distilled off
  2. dissolutionthe remaining viscous liquid dissolved in 200 mL of 2% NaOH
  3. customThe resulting bis-N-(1-methyl-2-hydroxyethyl)isophthalamide is then precipitated in acetone
  4. filtrationfiltered
  5. customdried
  6. temperatureThe mixture is then heated
  7. temperatureafter which time the homogenous yellow solution is cooled
  8. additionpoured into diethylether
  9. customto precipitate the 4,4'-dimethyl-2,2'-(1,3-phenylene)bis(oxazoline) hydrochloride salt
  10. extractionthe free base extracted into ether
  11. customThe organic phase is then dried
  12. customevaporated

Sources & evidence

ORD record
ord-6f5e37a2a8f04dcd89f7d60f6def9ba4
Source dataset
uspto-grants-1997_07
Patent number
US05644006

Linked notes

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