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

HRID 65930Notes

Reaction equation

HRID 65930 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][CH:10]([CH3:18])[N:9]2[CH:19]=1)([O:3][CH2:4][CH3:5])=[O:2].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22].[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:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]([CH3:18])[N:9]2[CH:19]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 227563592-Carbethoxy-5-methyl-5,6-dihydropyrrolo[1,2-c]quinazoline

Product 1

HCID 227563392,6-Dicarbethoxy-5-methyl-5,6-dihydropyrrolo[1,2-c]quinazoline

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of the product of Example XXXVIII (3.0 g, 0.0117 m) and ethyl chloroformate (12.6 g, 0.117 m) in acetone (50 ml) and H2O (50 ml) was treated with NaOH (0.21 ml aq. 30%) and the mixture refluxed for 1 hr. The acetone was removed in vacuo and the aqueous residue cooled in ice-bath. A solid formed and this was filtered, washed with water, and dried in vacuo. The crude product (3.4 g) was crystallized from methanol (25 ml) to afford the desired product; m.p. 125°-127°.

Workup

  1. temperaturethe mixture refluxed for 1 hr
  2. customThe acetone was removed in vacuo
  3. temperaturethe aqueous residue cooled in ice-bath
  4. customA solid formed
  5. filtrationthis was filtered
  6. washwashed with water
  7. customdried in vacuo
  8. customThe crude product (3.4 g) was crystallized from methanol (25 ml)

Sources & evidence

ORD record
ord-5c0313cb4ad24413969ec2ff7cd2ced4
Source dataset
uspto-grants-1978_12
Patent number
US04129653

Reaction notes

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