Dimethylformamide → HCID 21833472, compound

HRID 1740860Notes

Reaction equation

HRID 1740860 reaction equation
[OH:1][CH2:2][C:3]([N:5]([CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8])=[O:4].CN(C)C=O.[H-].[Na+].Cl[C:20]1[C:29]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[N:23]=[C:22]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[N:21]=1>C(Cl)(Cl)Cl>[F:36][C:33]1[CH:34]=[CH:35][C:30]([C:22]2[N:21]=[C:20]([O:1][CH2:2][C:3]([N:5]([CH2:9][CH2:10][CH3:11])[CH2:6][CH2:7][CH3:8])=[O:4])[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[N:23]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 138235672-Hydroxy-N,N-dipropylacetamideHCID 21833538HCID 21833538, compound

Product 1

HCID 21833472HCID 21833472, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-hydroxy-N,N-dipropylacetamide (1.8 g) and dimethylformamide (20 ml) is added sodium hydride (about 60% oily, 0.5 g) at 0 to 5° C., and the mixture is stirred at 0° C. for one hour. To the reaction mixture is added 4-chloro-2-(4-fluorophenyl)-5,6,7,8-tetrahydroquinazoline (2.0 g) at the same temperature, and the mixture is stirred at room temperature for four hours. To the mixture are added chloroform and ice-water, and the chloroform layer is collected, washed with water, 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 (2.2 g), m.p. 95-96° C.

Workup

  1. stirringthe mixture is stirred at room temperature for four hours
  2. customthe chloroform layer is collected
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel column chromatography (eluent; chloroform)
  7. customrecrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-353e52fd375346099c2afea2d33c6ce6
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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