p-Toluenesulfonic acid → HCID 136183437, compound

HRID 591746Notes

Reaction equation

HRID 591746 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[OH:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[C:28]([CH3:29])=[CH:27][C:24]([CH:25]=O)=[CH:23][C:22]=1[CH3:30].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[OH:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[C:28]([CH3:29])=[CH:27][C:24]([C:25]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[O:13][CH3:14])[N:1]=2)=[CH:23][C:22]=1[CH3:30]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium BisulfiteHCID 61669341HCID 61669341, compound

Product 1

HCID 136183437HCID 136183437, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2-amino-4,6-dimethoxy-benzamide (497 mg, 2.53 mmol) and 4-(4-hydroxybutoxy)-3,5-dimethyl benzaldehyde (660 mg, 2.53 mmol) in N,N-dimethyl acetamide (10 mL), NaHSO3 (58.5 wt %, 496 mg, 2.79 mmol) and p-TSA (96 mg, 0.50 mmol) were added and the reaction mixture was heated at 115° C. for 16 hours and then cooled to room temperature. The solvent was removed under reduced pressure. Water (100 mL) was added and stirred for 1 hour at room temperature. The solid separated was filtered and dried. The solid was further washed with diethyl ether to give product 2-[4-(4-hydroxy-butoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one as a white solid. Yield: 1.69 g (82%).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. additionWater (100 mL) was added
  4. customThe solid separated
  5. filtrationwas filtered
  6. customdried
  7. washThe solid was further washed with diethyl ether

Sources & evidence

ORD record
ord-bcac9f3aa7224203b08fca632ffcd590
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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