Toluene → HCID 21956528, compound

HRID 2213088Notes

Reaction equation

HRID 2213088 reaction equation
C1(C)C=CC=CC=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])=O.P(Cl)(Cl)(Cl)(Cl)Cl.[N-:40]=[N+:41]=[N-:42].[Na+]>CN(C=O)C>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:13]2[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N+:22]([O-:24])=[O:23])[N:42]=[N:41][N:40]=2)[CH:25]=[CH:26][C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 24819Phosphorus pentachlorideHCID 33557Sodium AzideHCID 21956525HCID 21956525, compound

Product 1

HCID 21956528HCID 21956528, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To toluene (1 mL) was added 3-methoxy-4-(pyridin-2-yl)-2′-nitrobenzanilide (97 mg, 0.28 mmol) and phosphorous pentachloride (56 mg, 0.27 mmol), and the mixture heated at reflux for 1 h. The resulting solution was cooled to rt and added to a solution of NaN3 (35 mg, 0.54 mmol) in DMF (2 mL). The mixture was heated at 90° C. for 1 h, cooled to rt, partitioned between EtOAc and water, and the organic layer concentrated. The crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (0:1 to 1:1) to afford 2-{2-methoxy-4-[1-(2-nitrophenyl)-1H-tetraazol-5-yl]phenyl}pyridine as a yellow solid.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was heated at 90° C. for 1 h
  4. temperaturecooled to rt
  5. custompartitioned between EtOAc and water
  6. concentrationthe organic layer concentrated
  7. customThe crude product was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (0:1 to 1:1)

Sources & evidence

ORD record
ord-ba9b9e5cd5ab4f52b7a7f716ee2e0011
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

Loading…