Ethyl Acetate → HCID 24807791, compound

HRID 1264906Notes

Reaction equation

HRID 1264906 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[F:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1.C(OCC)(=O)C>O1CCCC1.CCCCCC>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][C:13]1[N:42]([C:41]2[CH:43]=[CH:44][C:38]([F:37])=[CH:39][CH:40]=2)[C:18](=[O:20])[C:17]2[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 97314-FluoroanilineHCID 682631,1'-CarbonyldiimidazoleHCID 107113492-(2-Benzyloxycarbonylamino-acetylamino)-benzoic Acid

Product 1

HCID 24807791HCID 24807791, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of the benzoic acid (2) (180 mg, 0.55 mmol) in tetrahydrofuran (6 mL) was added 1,1′-carbonyldiimidazole (98 mg, 0.60 mmol). After a period of 2 h, 4-fluoroaniline (61 mg, 0.55 mmol) in tetrahydrofuran (1.5 mL) was added and the mixture was stirred at 75° C. overnight. The tetrahydrofuran was removed in vacuo and the residue was redissolved in ethyl acetate, washed with 10% aqueous hydrochloric acid, saturated aqueous sodium hydrogen carbonate, dried (MgSO4) and concentrated to give an oily residue which was subjected to silica-gel column chromatography [eluent: Ethyl acetate:Hexane, 20:80, v/v→60:40, v/v] to give the title quinazolinone (3) (0.11 g, 50%) as a white solid:

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. dissolutionthe residue was redissolved in ethyl acetate
  3. washwashed with 10% aqueous hydrochloric acid, saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give an oily residue which

Sources & evidence

ORD record
ord-096796c3ef5d4ea586f1c49d720ba89c
Source dataset
uspto-grants-2003_04
Patent number
US06545005B1

Reaction notes

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