Triethylamine → 4-{N-ethyl-N-[2-(2-methylphenoxy)ethyl]amino}-quinazoline

HRID 1659540

Reaction equation

HRID 1659540 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH2:12]([NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])[CH3:13].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:12]([N:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1)[CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 788644-ChloroquinazolineHCID 12797560N-Ethyl-2-(2-methylphenoxy)ethanamine

Product 1

HCID 127975614-{N-ethyl-N-[2-(2-methylphenoxy)ethyl]amino}-quinazolineYield 54.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2.5 g (0.015 mole) of 4-chloroquinazoline in toluene were added 2.7 g (0.015 mole) of N-ethyl-2-(2-methylphenoxy)ethylamine and 1.5 g (0.015 mole) of triethylamine. The mixture was then refluxed, with stirring, for 5.5 hours. After completion of the reaction, the toluene was removed from the reaction mixture by evaporation under reduced pressure. Water was then added to the residue and the mixture was extracted with chloroform and the extract was dried. The chloroform was removed by evaporation and the crystals which separated out were recrystallized from isopropanol, giving 2.5 g (54%) of the desired Compound No. 2, in the form of colourless prisms melting at 85°-87° C.

Workup

  1. temperatureThe mixture was then refluxed
  2. customAfter completion of the reaction
  3. customthe toluene was removed from the reaction mixture by evaporation under reduced pressure
  4. additionWater was then added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. customthe extract was dried
  7. customThe chloroform was removed by evaporation
  8. customthe crystals which separated out
  9. customwere recrystallized from isopropanol

Sources & evidence

ORD record
ord-3b6a51e5a21b4f02b5225e21ff2b1bf1
Source dataset
uspto-grants-1981_12
Patent number
US04304778

Linked notes

Loading…