Water → HCID 14460528, compound

HRID 1199656Notes

Reaction equation

HRID 1199656 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[C:17](Cl)[CH:18]=[CH:19][CH:20]=5)[C:15](=[O:23])[N:14]([CH3:24])[C:13]=34)[N:5]=2)[CH2:3][CH2:2]1.[Cl:25][C:26]1[CH:27]=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1.[H-].[Na+].O>CN(C)C=O.CCOCC>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[N:10]=[CH:11][N:12]4[C:21]5[C:16](=[C:17]([O:32][C:28]6[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[CH:27]=6)[CH:18]=[CH:19][CH:20]=5)[C:15](=[O:23])[N:14]([CH3:24])[C:13]=34)[N:5]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 79333-ChlorophenolHCID 24758Sodium hydrideHCID 14460518HCID 14460518, compound

Product 1

HCID 14460528HCID 14460528, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl-5-oxo-6-chloro-4,5-dihydro-imidazo(1,5-a)quinazoline (0.4 g, 1.2 mmol), 3-chlorophenol (0.4 g, 3 mmol), and sodium hydride (55% dispension in oil, 0.14 g, 3 mmol) in 20 ml of dry dimethylformamide was stirred for 8 h at 110° C., cooled to room temperature and poured into 30 ml of water and 5 ml of ether. The mixture was then stirred for 30 min. at 0° C. and the precipitate was filtered off, rinsed with water and dried giving 0.28 g (57%) of 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-4-methyl-5-oxo-6-(3-chlorophenoxy)-4,5-dihydroimidazo(1,5-a) quinazoline, M.p. 201°-203° C.

Workup

  1. temperaturecooled to room temperature
  2. stirringThe mixture was then stirred for 30 min. at 0° C.
  3. filtrationthe precipitate was filtered off
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-2d8119339b9c4329afd4ce9a610accf6
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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