Water → HCID 15871400, compound

HRID 1740855Notes

Reaction equation

HRID 1740855 reaction equation
Cl[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[NH2:18][CH2:19][C:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[O:21].C(N(CC)CC)C.O>C(Cl)(Cl)Cl>[C:12]1([C:4]2[N:3]=[C:2]([NH:18][CH2:19][C:20]([N:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[O:21])[C:11]3[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[N:5]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 127424812-amino-N,N-dipropyl-acetamideHCID 21833531HCID 21833531, compound

Product 1

HCID 15871400HCID 15871400, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-chloro-5,6,7,8-tetrahydro-2-phenylquinazoline (1.0 g), 2-amino-N,N-dipropylacetamide (0.78 g) and triethylamine (0.5 g) is refluxed with stirring at 150° C. for three hours. To the reaction mixture are added water and chloroform, and the chloroform layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; chloroform), and recrystallized from a mixture of diethyl ether and n-hexane to give the desired compound (1.3 g), m.p. 87-88° C.

Workup

  1. temperatureis refluxed
  2. customthe chloroform layer is separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  6. customrecrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-1621d87ecbe84bc6aacfb53cfbbf253d
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

Loading…