Acetic Acid → HCID 57465379, compound

HRID 1951591Notes

Reaction equation

HRID 1951591 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.C(O)(=O)C>[Zn]>[C:15]1([C:12]2[O:13][CH:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)[N:11]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 100614284-(4-nitrophenyl)-2-phenyloxazole

Product 1

HCID 57465379HCID 57465379, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

zinc dust (0.59 ml, 64 mmol) was added to a mixture of 4-(4-nitrophenyl)-2-phenyloxazole (1.13 g, 4.2 mmol) in acetic acid (20 ml, 349 mmol) at room temperature. An exotherm resulted. The reaction mixture was stirred at room temperature for 60 minutes then filtered, rinsing with ethyl acetate, and the filtrate concentrated under reduced pressure. The concentrate was slurried in toluene and concentrated under reduced pressure to afford a yellow solid (1.0 g, quantitative). ESI+ m/z=237.1 [MH]+.

Workup

  1. customAn exotherm resulted
  2. filtrationthen filtered
  3. washrinsing with ethyl acetate
  4. concentrationthe filtrate concentrated under reduced pressure
  5. concentrationconcentrated under reduced pressure
  6. customto afford a yellow solid (1.0 g, quantitative)

Sources & evidence

ORD record
ord-34a98f892ad14165b86c90592c7f7ecf
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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