HCID 57465370, compound → HCID 57465371, compound

HRID 1951577Notes

Reaction equation

HRID 1951577 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([C:21]([F:24])([F:23])[F:22])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Zn]>[C:15]1([C:13]2[N:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)[O:11][C:12]=2[C:21]([F:22])([F:23])[F:24])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 57465370HCID 57465370, compound

Product 1

HCID 57465371HCID 57465371, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

to a solution of 2-(4-nitrophenyl)-4-phenyl-5-(trifluoromethyl)oxazole (437 mg, 1307 μmol) in 20 mL acetic acid at room temperature was added zinc dust (1282 mg, 19611 μmol) all at once. An exotherm resulted. The mixture was stirred at room temperature for 2 hours then filtered. The filtrate was concentrated under reduced pressure, taken up in 25 mL toluene and concentrated under reduced pressure again to afford a yellow, foamy solid (350 mg, 88%). ESI+ m/z=305.0 [MH]+.

Workup

  1. customAn exotherm resulted
  2. filtrationthen filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure again

Sources & evidence

ORD record
ord-6ba458c3d7384be681a74bb94909a4e8
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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