HCID 23505601, compound → HCID 23505668, compound

HRID 1993312Notes

Reaction equation

HRID 1993312 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]3[O:16][CH2:15][CH2:14][O:13][C:10]=3[CH:11]=2)[CH:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:5][C:4]1=[S:23])[CH3:2]>C(Cl)(Cl)Cl.O=[Mn]=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]3[O:16][CH2:15][CH2:14][O:13][C:10]=3[CH:11]=2)[C:6]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:5][C:4]1=[S:23])[CH3:2]

Participants

4

Reactant 1

HCID 23505601HCID 23505601, compound

Product 1

HCID 23505668HCID 23505668, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 1-ethyl-6,7-ethylenedioxy-4-phenyl-3,4-dihydroquinazolin-2(1H)-thione (77 mg, 0.24 mmol) and MnO2 (180 mg, 2.07 mmol) in 5 mL of CHCl3 was stirred at rt for 3 days. The solids were filtered off and the solution concentrated in vacuo. The crude residue was subjected to flash column chromatography eluting with EtOAc:hexane to give the title compound (35 mg, 46%). 1H NMR (CDCl3): 7.72 (dd, 2H), 7.53-7.49 (m, 3H), 7.38 (s, 1H), 7.09 (3, 1H), 4.90 (m, 2H), 4.48-4.30 (m, 4H), 1.55 (t, 3H).

Workup

  1. filtrationThe solids were filtered off
  2. concentrationthe solution concentrated in vacuo
  3. washeluting with EtOAc

Sources & evidence

ORD record
ord-89eee74bd9014715be1e0b2c5740943b
Source dataset
uspto-grants-2010_01
Patent number
US07652006B2

Reaction notes

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