Water → 5-Cyano-2-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazoline

HRID 1939639Notes

Reaction equation

HRID 1939639 reaction equation
[C-:1]#[N:2].[K+].C1OCCOCCOCCOCCOCCOC1.Cl[C:23]1[N:32]2[CH:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:35]=[C:31]2[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[N:24]=1.O>C(#N)C>[C:1]([C:23]1[N:32]2[CH:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:35]=[C:31]2[C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[N:24]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 19367580HCID 19367580, compound

Product 1

HCID 193676095-Cyano-2-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazoline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 200 mg of potassium cyanide and 300 mg of 18-crown-6 in 20 mL of acetonitrile was added 5-Chloro-2-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazoline (220 mg). The mixture was refluxed for 2 hours, cooled and poured into water. The aqueous layer was extracted with dichloromethane, the organic layer separated and dried and the solvent removed in vacuo. The resultant crude reaction mixture was chromatographed using 15% ethyl acetate/hexane as eluent to yield 5-Cyano-2-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-c]-quinazoline (Compound 44), m.p. 203°-205° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. customthe organic layer separated
  5. customdried
  6. customthe solvent removed in vacuo
  7. customThe resultant crude reaction mixture
  8. customwas chromatographed

Sources & evidence

ORD record
ord-c4d4ebcc89974a8ca7e1481c8defea13
Source dataset
uspto-grants-1997_12
Patent number
US05696260

Reaction notes

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