Water → HCID 15583182, compound

HRID 2418212Notes

Reaction equation

HRID 2418212 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[NH:15][NH2:16])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[Cl:23][CH2:24][CH2:25][C:26](Cl)=[O:27].O>C(Cl)(Cl)Cl>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[C:5]1[NH:15][NH:16][C:26](=[O:27])[CH2:25][CH2:24][Cl:23])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 693643-Chloropropionyl chlorideHCID 3513570HCID 3513570, compound

Product 1

HCID 15583182HCID 15583182, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 4.50 g of 3-allyl-2-hydrazino-quinazolin-4(3H)-one (0.0208 mol) and 5.75 g of anhydrous potassium carbonate (0.0416 mol; 2 eq) in 100 ml of chloroform at room temperature as added 2.2 ml of 3-chloropropionyl chloride (2.91 g; 0.023 mol; 1.1 eq). Almost immediately, a precipitate appeared and after 1 hr, 50 ml of water were added to the stirred mixture to dissolve any potassium carbonate. The mixture was filtered and the product was washed twice with water then twice with ether, crystallized from ethanol and dried under vacuum over P2O5 at 80° C. to obtain 5.79 g (91% yield) of 3-allyl-2-(2-(3-chloropropionyl)hydrazino)quinazolin-4(3H)-one melting at 151°-153° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe product was washed twice with water
  3. customtwice with ether, crystallized from ethanol
  4. dry with materialdried under vacuum over P2O5 at 80° C.

Sources & evidence

ORD record
ord-0b5be28453834eb8a2aadbfef3b6d4ba
Source dataset
uspto-grants-1984_09
Patent number
US04472400

Reaction notes

Loading…