Triethylamine → 3-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-one

HRID 1654668Notes

Reaction equation

HRID 1654668 reaction equation
[CH2:1]([C:4]1[NH:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:5]=1)[CH2:2][CH3:3].C(N(CC)CC)C.[CH3:25][O:26][C:27]1[CH:42]=[CH:41][C:30]([CH:31](Cl)[C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:39][O:38][C:35]1[CH:34]=[CH:33][C:32]([CH:31]([N:13]2[C:12](=[O:14])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=3)[N:5]=[C:4]2[CH2:1][CH2:2][CH3:3])[C:30]2[CH:41]=[CH:42][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10706646bis(4-methoxyphenyl)chloromethaneHCID 135815037HCID 135815037, compound

Product 1

HCID 200766253-(4,4'-dimethoxybenzhydryl)-2-propyl-6-nitroquinazolin-4(3H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10.0 g (45 mmol) of 2-propyl-6-nitro-quinazolin-4(3H)-one in 160 ml of dry CH2Cl2 was added 9.5 ml (67 mmol) of triethylamine followed by 12.9 g (49 mmol) of 4,4'-dimethoxybenzhydryl chloride. The reaction mixture was stirred for 48 hours and then washed with 10% citric acid (2×20 ml), water (1×20 ml), saturated NaHCO3 (2×20 ml) and brine (1×20 ml). The solution was dried over MgSO4, filtered and concentrated in vacuo. The residue was recrystalised from EtOAc to give 17.3 g of white solid. 85% yield. 1H-NMR (CDCl3): 0.87 (t, 3H, J=7.3 Hz), 1.58 (bm, 2H), 2.72 (t, 2H, J=7.8 Hz), 3.80 (s, 6H), 6.88 (d, 4H, J=9 Hz), 7.19 (d, 4H, J=9.0 Hz), 7.73 (d, 1H, J=8.9 Hz), 8.48 (dd, 1H, J=2.8, 9.0 Hz), 9.08 (d, 1H, J=2.8 Hz).

Workup

  1. washwashed with 10% citric acid (2×20 ml), water (1×20 ml), saturated NaHCO3 (2×20 ml) and brine (1×20 ml)
  2. dry with materialThe solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystalised from EtOAc

Sources & evidence

ORD record
ord-98377aab86eb491ca2830f155fabfbb8
Source dataset
uspto-grants-1995_04
Patent number
US05409926

Reaction notes

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