Triethylamine → HCID 13910128, compound

HRID 231110Notes

Reaction equation

HRID 231110 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:18]=[C:17]([CH2:19][CH:20]([O:22][CH3:23])[CH3:21])[CH:16]=[CH:15][C:10]=1[O:11][CH2:12][CH2:13][NH2:14].Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][N:26]=1>C1(C)C=CC=CC=1>[CH3:8][C:9]1[CH:18]=[C:17]([CH2:19][CH:20]([O:22][CH3:23])[CH3:21])[CH:16]=[CH:15][C:10]=1[O:11][CH2:12][CH2:13][NH:14][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 788644-ChloroquinazolineHCID 20034504HCID 20034504, compound

Product 1

HCID 13910128HCID 13910128, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.0 g of triethylamine and 2.2 g of 2-[2-methyl-4-(2-methoxypropyl)phenoxy]ethylamine were added to 1.7 g of 4-chloroquinazoline dissolved in 50 ml of toluene. The mixture was then heated under reflux, whilst stirring, for 3 hours. At the end of this time, the reaction product was washed with water and dried over anhydrous sodium sulfate. Toluene was removed by distillation under reduced pressure. The oily product thus obtained was subjected to column chromatography (Wakogel C-200, eluted with a 1:1 by volume mixture of toluene and ethyl acetate) to isolate the product, and the crystals obtained were recrystallized from hexane, to give 2.2 g of the title compound as a colorless crystalline powder, melting at 95°-97° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux
  3. washAt the end of this time, the reaction product was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customToluene was removed by distillation under reduced pressure
  6. customThe oily product thus obtained
  7. washeluted with a 1:1 by volume mixture of toluene and ethyl acetate)
  8. customto isolate the product
  9. customthe crystals obtained
  10. customwere recrystallized from hexane

Sources & evidence

ORD record
ord-658ccb437fc74d5c9931f17ae3649811
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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