1-Bromo-3-chloropropane → HCID 15580741, compound

HRID 1701954Notes

Reaction equation

HRID 1701954 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]([CH3:18])[C:16](=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:21])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][CH2:25][Cl:26]>CS(C)=O>[Cl:26][CH2:25][CH2:24][CH2:23][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]([CH3:18])[C:16](=[O:19])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:20][CH3:21])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 13567258183722-02-5

Product 1

HCID 15580741HCID 15580741, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.8 gm (10 mmols) of 2-(4-hydroxy-phenyl)-3-methyl-6-methoxy-3,4-dihydro-quinazolin-4-one were dissolved in 20 ml of dimethylsulfoxide, and the solution was mixed, while stirring, with 1.35 gm (10 mmols+20%) of potassium tert. butylate. Subsequently, 2.8 ml of 1-bromo-3-chloropropane were added, and the mixture was stirred at room temperature until the reaction was complete. The reaction mixture was then poured into ice water, the aqueous mixture was extracted with ethyl acetate, and the combined organic extracts were evaporated in vacuo after drying over sodium sulfate. The resulting oil, which solidified into crystals, was recrystallized from acetone/ether.

Workup

  1. additionthe solution was mixed
  2. extractionthe aqueous mixture was extracted with ethyl acetate
  3. customthe combined organic extracts were evaporated in vacuo
  4. dry with materialafter drying over sodium sulfate
  5. customwas recrystallized from acetone/ether

Sources & evidence

ORD record
ord-f01d9aa6e0ef4fa88197092c40e8bd46
Source dataset
uspto-grants-1983_04
Patent number
US04379788

Reaction notes

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