Ethyl chloroformate → 2,6-Dicarbethoxy-5,6-dihydropyrrolo[1,2-c]quinazoline

HRID 65926Notes

Reaction equation

HRID 65926 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:11][CH2:10][N:9]2[CH:18]=1)([O:3][CH2:4][CH3:5])=[O:2].Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].[OH-].[Na+]>CC(C)=O.O>[C:1]([C:6]1[CH:7]=[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:10][N:9]2[CH:18]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 227563502-Carbethoxy-5,6-dihydropyrrolo[1,2-c]quinazoline

Product 1

HCID 125700262,6-Dicarbethoxy-5,6-dihydropyrrolo[1,2-c]quinazoline

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example IV (1.2 g, 0.005 m) and ethyl chloroformate (6.0 g, 0.0553 m) in acetone (20 ml) and H2O (50 ml) was treated with NaOH (0.1 ml aq. 30%) and the mixture stirred at room temperature for 15 min. The acetone was removed in vacuo and the aqueous residue cooled in an ice-bath. A solid formed and this was filtered, washed with water, and dried in vacuo. The crude product (1.0 g) was crystallized from methanol to afford the desired product; m.p. 80°-82° C.

Workup

  1. customThe acetone was removed in vacuo
  2. temperaturethe aqueous residue cooled in an ice-bath
  3. customA solid formed
  4. filtrationthis was filtered
  5. washwashed with water
  6. customdried in vacuo
  7. customThe crude product (1.0 g) was crystallized from methanol

Sources & evidence

ORD record
ord-351dad66b97341498fcf56c29e05b1a7
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

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