Triethylamine → HCID 12797562, compound

HRID 1659541Notes

Reaction equation

HRID 1659541 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.[CH3:12][NH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:12][N:13]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1)[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37732Methyl(2-phenoxyethyl)amineHCID 788644-Chloroquinazoline

Product 1

HCID 12797562HCID 12797562, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2.5 g (0.015 mole) of 4-chloroquinazoline in benzene were added 2.3 g (0.015 mole) of N-methyl-N-phenoxyethylamine and 1.5 g (0.015 mole) of triethylamine. The mixture was then refluxed, with stirring, for 7 hours. After completion of the reaction, the benzene was removed by evaporation. Water was added to the residue and the mixture was extracted with chloroform and the extract was dried. The chloroform was removed by evaporation and the resulting oil was purified by column chromatography through silica gel (eluted with a 1:1 by volume mixture of benzene and ethyl acetate) to give 3.7 g (88%) of the desired Compound No. 4 in the form of a pale yellow liquid having a refractive index nD27 1.6329.

Workup

  1. temperatureThe mixture was then refluxed
  2. customAfter completion of the reaction
  3. customthe benzene was removed by evaporation
  4. additionWater was 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 resulting oil was purified by column chromatography through silica gel (
  9. washeluted with a 1:1 by volume mixture of benzene and ethyl acetate)

Sources & evidence

ORD record
ord-8cd38802085142d78a0f947c67a68f60
Source dataset
uspto-grants-1981_12
Patent number
US04304778

Reaction notes

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