Benzocaine → 4-(4,5-dihydro-1,3-oxazol-2-yl)aniline

HRID 1978145Notes

Reaction equation

HRID 1978145 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=O)=[CH:4][CH:3]=1.CC([NH2:18])(C)CO.C1(C)C(C)=CC=CC=1.[NH2-].[Li+]>>[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]2[O:8][CH2:9][CH2:10][N:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 2337BenzocaineHCID 7237O-XyleneHCID 118072-Amino-2-methyl-1-propanolHCID 24532Lithium amide

Product 1

HCID 4239374-(4,5-dihydro-1,3-oxazol-2-yl)aniline

Procedure

Ethyl p-aminobenzoate, 20.65 g (0.125 mol), 2-methyl-2-aminopropanol, 22.3 g (0.25 mol) 150 ml of xylene, and 0.25 g of lithium amide were combined and heated at the reflux temperature for 50 hr. The alcohol and water liberated was collected in a Dean-Stark trap, providing indication when the reaction was complete. The xylene solvent was removed and the viscous liquid was added to water to precipitate the product. After drying, a 15.5 g (65%) yield of the 4,4-dimethyl derivative of 4-aminophenyl oxazoline was obtained. The product was recrystallized from ethyl acetate, giving white, crystalline material with mp 172° C. FT-IR, with peaks centered at 3445 (NH), 1635 (—C═N—), and 1602 (phenyl) cm−1 confirmed the desired amino functionalized oxazoline. Following the Example 6 procedure, TDO was used to covert the aforesaid compound to the desired acetoacetamide. The structure of this new composition is as follows:

Workup

  1. temperatureheated at the reflux temperature for 50 hr
  2. customThe alcohol and water liberated was collected in a Dean-Stark trap
  3. customproviding indication when the reaction
  4. customThe xylene solvent was removed
  5. additionthe viscous liquid was added to water
  6. customto precipitate the product
  7. customAfter drying

Sources & evidence

ORD record
ord-311d7be4f3994b4dabe17474f76ca7e1
Source dataset
uspto-grants-2001_05
Patent number
US06235901B1

Reaction notes

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