3-(2-chloroethyl)(1H,3H)quinazoline-2,4-dione → HCID 19981960, compound

HRID 1460454Notes

Reaction equation

HRID 1460454 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:15].[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)=[C:24]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[ClH:1].[F:37][C:34]1[CH:35]=[CH:36][C:31]([C:23]([C:20]2[CH:19]=[CH:18][C:17]([F:16])=[CH:22][CH:21]=2)=[C:24]2[CH2:30][CH2:29][CH2:28][N:27]([CH2:2][CH2:3][N:4]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[NH:6][C:5]3=[O:15])[CH2:26][CH2:25]2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 787663-(2-chloroethyl)(1H,3H)quinazoline-2,4-dioneHCID 516892Sodium BicarbonateHCID 19915768HCID 19915768, compound

Product 1

HCID 19981960HCID 19981960, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7.5 g of 3-(2-chloroethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline, 10 g of 4-[bis(4-fluorophenyl)methylene]perhydroazepine, 3.4 g of sodium hydrogen carbonate and 100 ml of toluene is brought to reflux for 12 hours. The mixture is filtered and concentrated under vacuum. The oil obtained is purified by chromatography on 500 g of 70-230 mesh silica using a mixture of dichloromethane, methanol and ammonia solution (98.4:1.5:0.1 V/V) as eluent.

Workup

  1. temperatureto reflux for 12 hours
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated under vacuum
  4. customThe oil obtained
  5. customis purified by chromatography on 500 g of 70-230 mesh silica using
  6. additiona mixture of dichloromethane, methanol and ammonia solution (98.4:1.5:0.1 V/V) as eluent

Sources & evidence

ORD record
ord-855721536ae246d8a43ce1faf8dd7620
Source dataset
uspto-grants-1991_12
Patent number
US05071847

Reaction notes

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