4-Hydroxybenzaldehyde → HCID 21960207, compound

HRID 1418995Notes

Reaction equation

HRID 1418995 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:17][C:18]1[N:27]([CH3:28])[C:26](=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1>CN(C=O)C.CCOC(C)=O>[CH3:28][N:27]1[C:26](=[O:29])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]1[CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 88996682-(chloromethyl)-3-methylquinazolin-4(3H)-one

Product 1

HCID 21960207HCID 21960207, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 4-hydroxybenzaldehyde (3.21 g, 26.3 mmol) and K2CO3 (3.64 g, 26.3 mmol) in dry DMF (50 ml) was stirred for 15 min at 30° C. To the above stirred mixture a solution of 2-chloromethyl-3-methyl4-oxo-3,4-dihydroquinazoline (5.0 g, 24.0 mmol) was added and stirred further for 90 minutes at the same temperature. The reaction mixture was diluted with EtOAc (200 ml), washed with aqueous Na2CO3 solution (3×50 ml) and then with brine, dried over anhydrous Na2SO4 and concentrated to yield the title compound (5.08 g, 72%).

Workup

  1. stirringstirred further for 90 minutes at the same temperature
  2. washwashed with aqueous Na2CO3 solution (3×50 ml)
  3. dry with materialwith brine, dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d88afedcfbb84b6dbe2d3488d8b51064
Source dataset
uspto-grants-1999_03
Patent number
US05885997

Reaction notes

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