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

HRID 1699098Notes

Reaction equation

HRID 1699098 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]>C(OCC)(=O)C.CO>[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

6

Reactant 3

HCID 7751Ethyl chloroacetateHCID 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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

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 ethyl chloroacetate (20 ml), and the reaction was carried out at an internal temperature of 140˜150° C. for 29 hours. This reaction mixture was cooled to ≦70° C., and after addition of ethyl acetate (20 ml) , a solvent mixture of methanol (30 ml) and ethyl acetate (20 ml) was added dropwise over about 30 minutes. After completion of dropwise addition, the mixture was worked up as in Example 1 to provide ethyl 2-(7-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-1-yl)acetate (13.60 g).

Workup

  1. customto give a concentrate
  2. temperatureThis reaction mixture was cooled to ≦70° C.
  3. additionwas added dropwise over about 30 minutes
  4. additionAfter completion of dropwise addition

Sources & evidence

ORD record
ord-6ae12abef50a4670b230df58611b446c
Source dataset
uspto-grants-2002_02
Patent number
US06344559B1

Reaction notes

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