Ethylamine → HCID 135430303, compound

HRID 365738Notes

Reaction equation

HRID 365738 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([NH2:18])[CH3:17]>C(O)CCC>[CH2:16]([NH:18][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 1356875047-Chloro-6-nitroquinazolin-4(1H)-one

Product 1

HCID 135430303HCID 135430303, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

7-Chloro-6-nitro-4(3H)-quinazolinone (20.0 g, 88.7 mmol) was suspended in n-butanol (150 ml), 70% aqueous ethylamine solution (120 ml) was added thereto, and the mixture was stirred for 15 minutes to give a clear solution which was then heated for 9 hours in a sealed tube in an oil bath (oil bath temperature set at 100° C. ). After the reaction was completed, the reaction mixture was left and cooled to precipitate yellow solids (first crystal) which were then filtered off. The first crystal was washed with methanol and ether and dried to give the desired title compound (8.27 g, 40%). The filtrate obtained at the time of acquisition of the first crystal was concentrated to precipitate crystal which was then filtered off and subjected to the same procedures as above to give second crystal as the desired title compound (5.84 g, 24%).

Workup

  1. customto give a clear solution which
  2. waitthe reaction mixture was left
  3. temperaturecooled
  4. customto precipitate yellow solids (first crystal) which
  5. filtrationwere then filtered off
  6. washThe first crystal was washed with methanol and ether
  7. customdried

Sources & evidence

ORD record
ord-7b17d115c4314ff5985f2092566ec707
Source dataset
uspto-grants-2000_10
Patent number
US06127541

Reaction notes

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