3-Chloropropionyl chloride → HCID 21465148, compound

HRID 1939942Notes

Reaction equation

HRID 1939942 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][NH:7][C:6]1=[O:15].[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>ClCCl>[Cl:16][CH2:17][CH2:18][C:19]([C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[NH:5][C:6](=[O:15])[NH:7][CH2:8]2)=[O:20]

Participants

5

Reactant 3

HCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 123607561,2,3,4-Tetrahydroquinazolin-2-one

Product 1

HCID 21465148HCID 21465148, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

20 g of aluminium chloride (0.15 mol) are taken up in 100 ml of dichloromethane. 7.43 g of 1,2,3,4-tetrahydroquinazolin-2-one (0.05 mol) are added in portions with stirring at a maximum of 20° C. The reaction mixture thus obtained is subsequently stirred for 30 minutes. A solution consisting of 6.98 g of 3-chloropropionyl chloride (0.055 mol) and 50 ml of dichloromethane is then added dropwise with stirring at a temperature of at most 25° C. and the mixture is subsequently stirred for a further hour. After completion of the reaction, the reaction mixture obtained is stirred into 300 g of ice, and the precipitate is filtered off with suction and washed with plenty of water and small amounts of methanol. The reaction forms a slightly more polar product than the starting material, which can be separated by thin-layer chromatography using an eluent consisting of chloroform and methanol in the mixture ratio 95:5. Yield: 11.37 g of 6-(3-chloro-1-oxopropyl)-1,2,3,4-tetrahydroquinazolin-2-one (95.3% of theory); m.p: >270° C.

Workup

  1. customThe reaction mixture thus obtained
  2. stirringis subsequently stirred for 30 minutes
  3. additionis then added dropwise
  4. stirringwith stirring at a temperature of at most 25° C.
  5. stirringthe mixture is subsequently stirred for a further hour
  6. customAfter completion of the reaction
  7. customthe reaction mixture obtained
  8. filtrationthe precipitate is filtered off with suction
  9. washwashed with plenty of water and small amounts of methanol
  10. customcan be separated by thin-layer chromatography

Sources & evidence

ORD record
ord-3e458859effa4d358524dd3770ee8bbf
Source dataset
uspto-grants-1997_12
Patent number
US05698553

Reaction notes

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