Ethyl chloroformate → 2-hydroxy-3-[3-(1H-imidazol-1-yl)propyl]quinazolin-4(3H)-one

HRID 1788684Notes

Reaction equation

HRID 1788684 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)=[O:5].Cl[C:20](OCC)=[O:21]>C(O)C>[N:10]1([CH2:9][CH2:8][CH2:7][N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:1][C:20]2=[O:21])[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 27983352-amino-N-(3-imidazol-1-ylpropyl)benzamide

Product 1

HCID 139527692-hydroxy-3-[3-(1H-imidazol-1-yl)propyl]quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 g of 2-amino-N-[3-(1H-imidazol-1-yl)propyl]benzamide and 15 ml of ethyl chloroformate was heated in an oil bath at 95°-105° C. for 1.5 hours, dissolved in 50 ml of ethanol, and concentrated. The residue was mixed with 100 ml of ethanol and 3.2 g of potassium hydroxide, heated at reflux temperature for 3 hours and concentrated. The residue was dissolved in water and acidified with acetic acid to pH 6-7. The white precipitate was separated by filtration and recrystallized from ethanol. The desired product melted at 197°-200° C.

Workup

  1. temperaturewas heated in an oil bath at 95°-105° C. for 1.5 hours
  2. concentrationconcentrated
  3. additionThe residue was mixed with 100 ml of ethanol and 3.2 g of potassium hydroxide
  4. temperatureheated
  5. temperatureat reflux temperature for 3 hours
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in water
  8. customThe white precipitate was separated by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e6e5308386f14afbbdcf8015ffa02749
Source dataset
uspto-grants-1987_08
Patent number
US04684654

Reaction notes

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