p-Toluenesulfonic acid → BAS 00699730

HRID 1469216Notes

Reaction equation

HRID 1469216 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=O)[O:4][C:2]2=O.[Cl:13][C:14]1[CH:21]=[CH:20][C:17](C=O)=[CH:16][CH:15]=1.C([O-])(=O)C.[NH4+:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:5]2[NH:26][C:2](=[O:4])[C:1]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 77264-ChlorobenzaldehydeHCID 8359Isatoic AnhydrideHCID 517165Ammonium Acetate

Product 1

HCID 2807156BAS 00699730

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Isatoic anhydride (163 mg, 10 003|\ was dissolved under an argon atmosphere in 5 ml of ethanol and, after addition of 4-chlorobenzaldehyde (211 mg, 15 mmol), ammonium acetate (93 mg, 12 mmol) and 4-toluenesulfonic acid (86 mg, 5 mmol), boiled at reflux for 5 hours. The product precipitated in the course of cooling. The precipitated solid was washed with a little ethanol and dried. This gave 150 mg (54.5% of theory) of 2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one as a white solid of melting point 190° C. 1H NMR (400 MHz, CDCl3 δ, ppm) 7.95 (d, 1H), 7.55 (dd, 2H), 7.42 (dd, 2H), 7.34 (t, 1H), 6.91 (t, 1H), 6.68 (d, 1H), 5.90 (s, 1H), 5.75 (br. S, 1H), 4.35 (br. S, 1H).

Workup

  1. temperatureat reflux for 5 hours
  2. customThe product precipitated in the course
  3. temperatureof cooling
  4. washThe precipitated solid was washed with a little ethanol
  5. customdried

Sources & evidence

ORD record
ord-86539b36b9114bfe8675a1514f907e03
Source dataset
uspto-grants-2015_04
Patent number
US09006265B2

Reaction notes

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