Ethyl chloroacetate → Ethyl (7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetate

HRID 1699100Notes

Reaction equation

HRID 1699100 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.ClC1C=C2C(C(O[Si](C)(C)C)=NC(O[Si](C)(C)C)=N2)=CC=1.Cl[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].[Br-].[Li+]>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[NH:7][C:8](=[O:12])[N:9]2[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 7751Ethyl chloroacetateHCID 82050Lithium BromideHCID 2468587-Chloroquinazoline-2,4-diolHCID 118240197-Chloro-2,4-bis(trimethylsilyloxy)quinazoline

Product 1

HCID 9838691Ethyl (7-chloro-2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)acetate

Procedure

7-Chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazoline (10 g) was treated as in Example 1 to give a concentrate containing 7-chloro-2,4-bis(trimethylsilyloxy)quinazoline. To this concentrate was added an oil prepared from ethyl chloroacetate (15 ml) and lithium bromide (2.21 g), and the reaction was carried out at an internal temperature of 115˜130° C. for 18 hours. This reaction mixture was cooled to ≦70° C. and worked up as in Example 4 to provide ethyl 2-(7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-1-yl)acetate (13.66 g).

Workup

  1. customto give a concentrate
  2. additionTo this concentrate was added an oil
  3. temperatureThis reaction mixture was cooled to ≦70° C.

Sources & evidence

ORD record
ord-b3c2aa4fd78441caab5603db06dd2618
Source dataset
uspto-grants-2002_02
Patent number
US06344559B1

Reaction notes

Loading…