p-Toluenesulfonic acid → HCID 136038021, compound

HRID 336701Notes

Reaction equation

HRID 336701 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH3:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([CH3:25])[C:23]=1[OH:24])[CH:19]=O.S([O-])(O)=O.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C.O>[OH:24][C:23]1[C:22]([CH3:25])=[CH:21][C:18]([C:19]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[C:8]([O:13][CH3:14])[CH:7]=3)[N:1]=2)=[CH:17][C:16]=1[CH3:15]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 108672362-Amino-4,5-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 136038021HCID 136038021, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 2-amino-4,5-dimethoxybenzamide (0.157 g, 0.8 mmol) in N,N-dimethylacetamide (5 mL) were added 3,5-dimethyl-4-hydroxybenzaldehyde (0.120 g, 0.8 mmol), sodium hydrogen sulphite (58.5%, 0.156 g, 0.88 mmol) and p-toluenesulfonic acid (15 mg, 0.08 mmol). The reaction mixture was stirred at 150° C. for 3 h. The reaction mixture was cooled to room temperature and water (40 mL) was added. A white precipitate was formed and filtered off, washed with water and a small amount of methanol and dried under vacuum to give 2-(4-hydroxy-3,5-dimethylphenyl)-6,7-dimethoxyquinazolin-4(3H)-one (0.230 g, 88% yield) as an off-white solid. Selected data: MS (ES) m/z: 327.12; MP>300° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customA white precipitate was formed
  3. filtrationfiltered off
  4. washwashed with water
  5. dry with materiala small amount of methanol and dried under vacuum

Sources & evidence

ORD record
ord-05ff1303eb404b2ea446f81bc4712c07
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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