Ethanol → HCID 13309031, compound

HRID 544544Notes

Reaction equation

HRID 544544 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:15])[CH:11]=2)[N:6]=[C:5]1Cl.C(O)C.[CH2:20]([NH2:23])[CH:21]=[CH2:22].CCCCC>CC(N(C)C)=O.O>[CH2:20]([N:23]1[C:5]2=[N:6][C:7]3[C:12]([C:13](=[O:14])[N:4]2[CH2:3][CH2:2]1)=[CH:11][C:10]([Cl:15])=[CH:9][CH:8]=3)[CH:21]=[CH2:22]

Participants

7

Reactant 4

HCID 702EthanolHCID 7853AllylamineHCID 8003PentaneHCID 13309030HCID 13309030, compound

Product 1

HCID 13309031HCID 13309031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent3×

Procedure

A solution of 1.0 g. of 3-(2-chloroethyl)-2,6-dichloro-3,4-dihydroquinazolin-4-one in 50 ml. of ethanol is combined with a solution of 0.62 g. of allylamine in 10 ml of dimethylacetamide and the resulting mixture heated to reflux with dimethylacetamide being added as required to dissolve any remaining solid starting material. After heating at reflux for about 5 hours the resulting reaction mixture is allowed to cool, the mixture stripped down to a dimethylacetamide slurry and pentane added. A white solid form which dissolves upon addition of water after which the organic layer is dried and concentrated in vacuo to a solid residue which is washed with pentane to obtain 1-allyl-7-chloro-2,3-dihydro-imidazo[2,1-b]quinazolin-5(1H)-one, m.p. 91°-93° C.

Workup

  1. additionadded
  2. dissolutionto dissolve any remaining solid
  3. temperatureAfter heating
  4. temperatureat reflux for about 5 hours
  5. customthe resulting reaction mixture
  6. temperatureto cool
  7. additionadded
  8. customis dried
  9. concentrationconcentrated in vacuo to a solid residue which
  10. washis washed with pentane

Sources & evidence

ORD record
ord-1a25619dd2f94a9f965816aa6f082540
Source dataset
uspto-grants-1984_05
Patent number
US04451448

Reaction notes

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