Pyridine → HCID 23025571, compound

HRID 1437478Notes

Reaction equation

HRID 1437478 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=3)[C:12]([NH2:14])=O)[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O>O>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=3)[C:12]#[N:14])[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 23025706HCID 23025706, compound

Product 1

HCID 23025571HCID 23025571, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-(6-bromobenzoxazol-2-yl)benzamide (Compound of Example 253) (1.09 g), pyridine (0.41 g) and N,N-dimethyl formamide (20 ml) was added dropwise oxalyl chloride (0.52 g) at 0° C., and the mixture was stirred at 0° C. for 50 minutes. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and water, successively, and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain 3-(6-bromobenzoxazol-2-yl)benzonitrile (949 mg, 92%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1 N hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium bicarbonate and water, successively, and dried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-982393458c9e4a7b8d35d68f156be9e8
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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