Triethylamine → 4-fluoro-N-(4-methoxy-7-phenyl-benzooxazol-2-yl)-benzamide

HRID 1611935Notes

Reaction equation

HRID 1611935 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[O:11][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1>CN(C1C=CN=CC=1)C.C1COCC1>[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:12][C:10]2[O:11][C:7]3[C:6]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:32])=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 222522314-Methoxy-7-phenyl-benzooxazol-2-ylamine

Product 1

HCID 100215224-fluoro-N-(4-methoxy-7-phenyl-benzooxazol-2-yl)-benzamideYield 33%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 100 mg (0.42 mmol) 4-methoxy-7-phenyl-benzooxazol-2-ylamine, 0.087 ml (0.62 mmol) triethylamine and 5.1 mg N,N-dimethyl-4-aminopyridine in 5 ml THF at room temperature was added dropwise a solution of 0.064 ml (0.54 mmol) 4-fluoro-benzoyl chloride in 2 ml THF and stirring continued at 65° C. for 16 h. The reaction mixture was then concentrated in vacuo. To the residue was added water, and the mixture was extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/4 then 4/1 ethyl acetate/hexane) followed by trituration in ether afforded 50 mg (33%) 4-fluoro-N-(4-methoxy-7-phenyl-benzooxazol-2-yl)-benzamide as a light yellow crystalline solid. EI-MS m/e (%): 362 (M+, 90), 123 ([FC6H4CO+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionTo the residue was added water
  3. extractionthe mixture was extracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fd4ea1107d8442d928b518260862d19
Source dataset
uspto-grants-2006_01
Patent number
US06992083B2

Reaction notes

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