p-Toluenesulfonic acid monohydrate → HCID 136038033, compound

HRID 1498669Notes

Reaction equation

HRID 1498669 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].[CH:15]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([NH2:25])=[O:24])=[CH:19][CH:18]=1)=O.S([O-])(O)=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:6][C:15]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][C:23]([NH2:25])=[O:24])=[CH:19][CH:18]=1)=[N:1]2

Participants

6

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 6016302-(4-formylphenoxy)acetamideHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

Product 1

HCID 136038033HCID 136038033, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-Amino-4,6-dimethoxy-benzamide (150 mg, 0.764 mmol), 2-(4-formyl-phenoxy)-acetamide (137 mg, 0.764 mmol), sodium hydrogen sulfite (150 mg, 58.5%) and p-toluenesulfonic acid monohydrate (15 mg) in N,N-dimethyl acetamide (15 mL) were heated to 150° C. overnight. N,N-dimethyl acetamide was removed under vacuum and the residue was poured into water (50 mL). The solid was filtered off and washed with methanol to yield 2-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)phenoxy)acetamide (74 mg, 27.2%). Selected data: MS (m/z): 356.09; MP 309-311° C. HPLC purity: 88.57%.

Workup

  1. customN,N-dimethyl acetamide was removed under vacuum
  2. additionthe residue was poured into water (50 mL)
  3. filtrationThe solid was filtered off
  4. washwashed with methanol

Sources & evidence

ORD record
ord-af5a92ddf83243dab68bb6222f42b9a9
Source dataset
uspto-grants-2015_12
Patent number
US09199990B2

Reaction notes

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