4-Hydroxybenzaldehyde → HCID 21960207, compound

HRID 2211455Notes

Reaction equation

HRID 2211455 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-methyl-4-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-758f954820f04b139e444eadcf56c573
Source dataset
uspto-grants-2006_09
Patent number
USRE039266E1

Reaction notes

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