1,1'-Carbonyldiimidazole → 1-Phenyl-5-phenoxy-3,4-dihydro-(1H)-quinazolin-2-one

HRID 1826835Notes

Reaction equation

HRID 1826835 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCCC1>[C:17]1([N:16]2[C:12]3[C:9](=[C:8]([O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:15]=[CH:14][CH:13]=3)[CH2:10][NH:11][C:23]2=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 221362242-Phenoxy-6-(phenylamino)benzylamine

Product 1

HCID 98617161-Phenyl-5-phenoxy-3,4-dihydro-(1H)-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product of example 1c above, 2-phenoxy-6-(phenylamino)benzyl amine, (0.165 g 0.57 mmol) was dissolved in dry tetrahydrofuran (5 mL) and stirred under argon at room temperature. 1,1′-Carbonyldiimidazole (0.120 g, 0.74 mmol) dissolved in dry tetrahydrofuran (2 mL) was added and the mixture stirred at room temperature. The solvent was evaporated in vacuo, to give the crude product which was flash chromatographed on silica gel eluted with 0–2% methanol in methylene chloride to give to the title compound as a white amorphous solid. mp 225–227° C.

Workup

  1. additionwas added
  2. stirringthe mixture stirred at room temperature
  3. customThe solvent was evaporated in vacuo
  4. customto give the crude product which
  5. customchromatographed on silica gel
  6. washeluted with 0–2% methanol in methylene chloride

Sources & evidence

ORD record
ord-f69158d16e4d45d1aab76335f5715877
Source dataset
uspto-grants-2006_05
Patent number
US07053099B1

Reaction notes

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