HCID 13769154, compound → HCID 13769155, compound

HRID 2232501Notes

Reaction equation

HRID 2232501 reaction equation
[C:1]1([C:7]2[N:16]=[C:15]([CH2:17][CH2:18][C:19]([O:21]CC)=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(NCC)C>[CH2:7]([N:8]([CH2:9][CH3:10])[C:19](=[O:21])[CH2:18][CH2:17][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:16]=1)[CH3:1]

Participants

3

Reactant 1

HCID 13769154HCID 13769154, compound

Product 1

HCID 13769155HCID 13769155, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of ethyl 2-phenyl-4-quinazolinepropionate (4.3 g) and diethylamine (30 cc) is heated to 250°C. for 40 hours. After the mixture is cooled, the excess diethylamine is evaporated off. The residue is chromatographed on silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant. The product (3.2 g) is recovered and recrystallized in isopropyl ether. N,N-Diethyl-2-phenyl-4-quinazolinepropanamide (2.2 g), m.p. 103° C., is obtained.

Workup

  1. temperatureAfter the mixture is cooled
  2. customthe excess diethylamine is evaporated off
  3. customThe residue is chromatographed on silica gel with a cyclohexane/ethyl acetate (1:1 by volume) mixture as eluant
  4. customThe product (3.2 g) is recovered
  5. customrecrystallized in isopropyl ether

Sources & evidence

ORD record
ord-1fb4c9c2e7f745c88af2c11f0d0a7c0d
Source dataset
uspto-grants-1988_11
Patent number
US04788199

Reaction notes

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