p-Bromochlorobenzene → HCID 23336425, compound

HRID 903549Notes

Reaction equation

HRID 903549 reaction equation
C1([Mg]Br)C=CC=CC=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1.[Mg].[CH3:18][N:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:29])[N:21]2[CH2:30][CH2:31][N:32]=[C:20]12>O1CCCC1.O.C(OCC)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:22]2([OH:29])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:19]([CH3:18])[C:20]3=[N:32][CH2:31][CH2:30][N:21]23)=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 7806p-BromochlorobenzeneHCID 731601HCID 731601, compoundHCID 5462224MagnesiumHCID 178418255HCID 178418255, compound

Product 1

HCID 23336425HCID 23336425, compoundYield 26.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a phenylmagnesium bromide solution prepared from 6.9 g of p-chlorophenyl bromide, 0.88 g of magnesium and 25 ml of dry diethyl ether was added dropwise a solution of 2.42 g of 10-methyl-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline-5-one in 30 ml of dry tetrahydrofuran with stirring and ice-cooling. The mixture was heated under reflux for 2 hours and then cooled. To the mixture were added dropwise 20 ml of water and stirring was continued for a while. The resulting mixture was extracted with hot chloroform and the insoluble material was filtered off and washed with hot chloroform. The chloroform layer was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was crystallized from ethanol and the crystals were further recrystallized from dimethylformamide to give 1.0 g of 5-(p-chlorophenyl)-5-hydroxy-10-methyl-2,3,5,10-tetrahydroimidazo[2,1-b]quinazoline as colorless needles, m.p. 207°-209° C. (decomp.).

Workup

  1. temperatureice-cooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. temperaturecooled
  5. stirringstirring
  6. extractionThe resulting mixture was extracted with hot chloroform
  7. filtrationthe insoluble material was filtered off
  8. washwashed with hot chloroform
  9. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  10. concentrationconcentrated to dryness under reduced pressure
  11. customThe residue was crystallized from ethanol
  12. customthe crystals were further recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-fc07e85cd0424333aa0a951db1c5204b
Source dataset
uspto-grants-1980_10
Patent number
US04228167

Reaction notes

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