Acetyl chloride → HCID 57940883, compound

HRID 1437480Notes

Reaction equation

HRID 1437480 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=3)[NH2:12])[O:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[O:25]1CC[CH2:27][CH2:26]1.C(Cl)(=O)C>O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([NH:12][C:26](=[O:25])[CH3:27])[CH:13]=[CH:14][CH:15]=3)[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 23025926HCID 23025926, compound

Product 1

HCID 57940883HCID 57940883, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-(6-bromobenzoxazol-2-yl)aniline (Compound of Example 267) (925 mg), triethylamine (390 mg) and tetrahydrofuran (35 ml) was added acetyl chloride (276 mg) at room temperature. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). 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 N-[3-(6-bromobenzoxazol-2-yl)phenyl]acetamide (923 mg, 87%).

Workup

  1. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  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-c78d536c1d22480c98ae42535a555ae1
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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