Triethylamine → 4-(5-Chloropentylamino)-7-ethylamino-6-nitroquinazoline

HRID 2258432Notes

Reaction equation

HRID 2258432 reaction equation
C(N(CC)CC)C.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]O.Cl[C:16]1[C:25]2[C:20](=[CH:21][C:22]([NH:29][CH2:30][CH3:31])=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=2)[N:19]=[CH:18][N:17]=1.S(Cl)([Cl:34])=O>ClCCCl.O1CCOCC1>[Cl:34][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:16]1[C:25]2[C:20](=[CH:21][C:22]([NH:29][CH2:30][CH3:31])=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=2)[N:19]=[CH:18][N:17]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 756345-Aminopentan-1-olHCID 232929894-Chloro-7-ethylamino-6-nitroquinazoline

Product 1

HCID 229218864-(5-Chloropentylamino)-7-ethylamino-6-nitroquinazolineYield 93.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (14.9 ml, 106.9 mmol) and 5-amino-1-pentanol (2.47 ml, 22.7 mmol) were added to a 1,4-dioxane solution (100 ml) of 4-chloro-7-ethylamino-6-nitroquinazoline (5.74 g, 22.7 mmol) obtained in Reference Example 13 under ice-cooling and the mixture was stirred at room temperature for 19 hours. The precipitated solid was filtered off, washed successively with water and ether and dried. To a solution of the resulting solid in 1,2-dichloroethane (40 ml), thionyl chloride (4.80 ml, 65.8 mmol) was added and the mixture was heated under reflux for 3 hours. After the solvent was distilled off, ice and a saturated aqueous solution of sodium bicarbonate were added and the mixture was extracted with chloroform. The organic layer was dried over a drying agent (magnesium sulfate), the drying agent was filtered off and the filtrate was concentrated under reduced pressure to give 7.15 g (93.3%) of the title compound as a crude product.

Workup

  1. customobtained in Reference Example 13 under ice-
  2. temperaturecooling
  3. filtrationThe precipitated solid was filtered off
  4. washwashed successively with water and ether
  5. customdried
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 3 hours
  8. distillationAfter the solvent was distilled off
  9. additionice and a saturated aqueous solution of sodium bicarbonate were added
  10. extractionthe mixture was extracted with chloroform
  11. dry with materialThe organic layer was dried over a drying agent (magnesium sulfate)
  12. filtrationthe drying agent was filtered off
  13. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0da142b53d28412c85749e8568035ae0
Source dataset
uspto-grants-1997_08
Patent number
US05661147

Reaction notes

Loading…