Water → HCID 15583181, compound

HRID 2418211Notes

Reaction equation

HRID 2418211 reaction equation
[NH:1]([C:3]1[N:12]([CH2:13][CH2:14][CH3:15])[C:11](=[O:16])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[Cl:17][CH2:18][C:19](Cl)=O.O.C(OCC)(=O)C>CN(C)C=O.ClCCl>[Cl:17][CH2:18][C:19]1[N:4]2[C:5]3[C:10]([C:11](=[O:16])[N:12]([CH2:13][CH2:14][CH3:15])[C:3]2=[N:1][N:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

7

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8857Ethyl AcetateHCID 15583179HCID 15583179, compound

Product 1

HCID 15583181HCID 15583181, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

156 g of 2-hydrazino-3-n-propylquinazolin-4(3H)-one (0.72 mole) were suspended in 500 ml of dimethylformamide and 90 g of chloroacetyl chloride (0.80 mole) were added in portions with cooling in an ice bath. When the addition was complete, the mixture was heated on a hot water bath for three hours until TLC (SiO2EtOAc) indicated no starting material or intermediate remaining. The resultant mixture was poured into one liter of water and one liter of ethyl acetate and 500 ml of dichloromethane and the organic and aqueous layers were separated. The aqueous layer was extracted twice more with 500 ml of ethyl acetate and the combined organic layers were extracted twice with 500 ml of water, dried over MgSO4, filtered and evaporated to dryness. The crystalline residue was triturated with ether, filtered, washed with ether and dried under vacuum over P2O5 to obtain 146 g (74% yield) of the 1-chloromethyl-4-n-propyl[1,2,4]triazolo[4,3-a]-quinazolin-5(4H)-one melting at (capillary) 141°-145° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. additionWhen the addition
  3. temperaturethe mixture was heated on a hot water bath for three hours until TLC (SiO2EtOAc)
  4. customthe organic and aqueous layers were separated
  5. extractionThe aqueous layer was extracted twice more with 500 ml of ethyl acetate
  6. extractionthe combined organic layers were extracted twice with 500 ml of water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crystalline residue was triturated with ether
  11. filtrationfiltered
  12. washwashed with ether
  13. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-0e88363393144432a8688be02c4ddb1b
Source dataset
uspto-grants-1984_09
Patent number
US04472400

Reaction notes

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