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p-Toluenesulfonic acid → 2-(3,5-dimethyl-4-(2-morpholinoethoxy)phenyl)quinazolin-4(3H)-one

HRID 336681
Notes
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Reaction equation

HRID 336681 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([CH3:29])[C:19]=1[O:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[CH:15]=O.S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C.O>[CH3:29][C:18]1[CH:17]=[C:14]([C:15]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:1]=2)[CH:13]=[C:12]([CH3:11])[C:19]=1[O:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6942AnthranilamideHCID 23665763Sodium BisulfiteHCID 289325803,5-Dimethyl-4-(2-morpholin-4-yl-ethoxy)benzaldehyde

Product 1

HCID 1360380282-(3,5-dimethyl-4-(2-morpholinoethoxy)phenyl)quinazolin-4(3H)-oneYield 50.1%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-amino benzamide (136 mg, 1.0 mmol) in N,N-dimethyl acetamide (5 mL) were added 3,5-dimethyl-4-(2-morpholin-4-yl-ethoxy)benzaldehyde (263 mg, 1.0 mmol), sodium hydrogen sulphite (58.5%) (196 mg, 1.1 mmol) and p-toluenesulfonic acid (19 mg, 0.1 mmol). The reaction mixture was stirred at 150° C. overnight. Water (40 mL) was added. The formed solid was filtered off, washed with water and a small amount of methanol and dried under vacuum to give the title compound (190 mg, 50%) as an off-white solid. To a solution of the above compound (174 mg, 0.458 mmol) in 2:1 anhydrous CH2Cl2-methanol (15 mL) was added 1.0 M solution of hydrogen chloride in ether (1.5 mL) and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed under reduced pressure. The residue was triturated with 10% methanol in anhydrous ether to give the hydrochloride of 2-(3,5-dimethyl-4-(2-morpholinoethoxy)phenyl)quinazolin-4(3H)-one (187 mg, 98%), as an off-white solid. Selected data: MS (ES) m/z: 380.10; MP 300-302° C. (hydrochloride).

Workup

  1. filtrationThe formed solid was filtered off
  2. washwashed with water
  3. dry with materiala small amount of methanol and dried under vacuum

Sources & evidence

ORD record
ord-770a583180a44e45a8aab4829328bf03
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889698B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes