p-Toluenesulfonic acid monohydrate → 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

HRID 591767Notes

Reaction equation

HRID 591767 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([CH3:13])=[CH:11][C:8]([CH:9]=O)=[CH:7][C:6]=1[CH3:14].[NH2:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:17]=1[C:18]([NH2:20])=[O:19].S(=O)(O)[O-].[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[Cl:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:16]2[C:17]=1[C:18](=[O:19])[NH:20][C:9]([C:8]1[CH:11]=[C:12]([CH3:13])[C:5]([O:4][CH2:3][CH2:2][OH:1])=[C:6]([CH3:14])[CH:7]=1)=[N:15]2

Participants

6

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136759682-Amino-6-chlorobenzamideHCID 23665763Sodium BisulfiteHCID 289325784-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde

Product 1

HCID 1361833855-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-(2-Hydroxyethoxy)-3,5-dimethylbenzaldehyde (0.70 g, 3.58 mmol), 2-amino-6-chlorobenzamide (0.60 g, 3.51 mmol), sodium bisulfite (0.71 g, 3.86 mmol) and p-toluenesulfonic acid monohydrate (0.133 g, 0.699 mmol) in anhydrous N,N-dimethyl acetamide (14 mL) were heated at 120° C. under nitrogen for 23 hours. The solvent was evaporated and the white solid was triturated with water (50 mL), filtered, and washed with water (20 mL). The solid was dried in vacuo and triturated with Et2O (20 mL), filtered, and dried to give 5-chloro-2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one as a white solid. Yield: 0.77 g, (64%).

Workup

  1. customThe solvent was evaporated
  2. customthe white solid was triturated with water (50 mL)
  3. filtrationfiltered
  4. washwashed with water (20 mL)
  5. customThe solid was dried in vacuo
  6. customtriturated with Et2O (20 mL)
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-a921b621b43c42b2bb34f1ae050ee835
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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