Acetyl chloride → HCID 4155152, compound

HRID 1723359Notes

Reaction equation

HRID 1723359 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15](Cl)(=[O:17])[CH3:16]>N1C=CC=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2795744'-Bromo-[1,1'-biphenyl]-4-amine

Product 1

HCID 4155152HCID 4155152, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

[I] A solution prepared by dissolving 0.75 g of 4-amino-4'-bromobiphenyl in 10 ml of pyridine, was cooled with ice, and 1.0 g of acetyl chloride was dropwise added thereto. The mixture was stirred over a period of 30 minutes. After the completion of the reaction, the reaction solution was extracted with ethyl acetate and water. The organic layer was washed with dilute hydrochloric acid and further with a saturated sodium chloride aqueous solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.8 g of N-(4'-bromo-4-biphenylyl)acetamide as colorless crystals. [II] A solution prepared by dissolving 0.80 g of N-(4'-bromo-4-biphenylyl)acetamide obtained in step [I] in 10 ml of dimethylformamide, was dropwise added at a temperature of from 15° to 20° C. to 10 ml of a dimethylsulfoxide solution in which 0.17 g of sodium hydride (60% nujol mixture) was suspended. After the dropwise addition, the mixture was stirred at room temperature for 30 minutes, and then 0.78 g of methyl iodide was dropwise added thereto at a temperature of from 15° to 20° C. Then, the mixture was stirred for 3 hours at room temperature.

Workup

  1. custom[I] A solution prepared
  2. additionwas dropwise added
  3. customAfter the completion of the reaction
  4. extractionthe reaction solution was extracted with ethyl acetate and water
  5. washThe organic layer was washed with dilute hydrochloric acid and further with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ac25cd8d7f064c6bbfd2c1a8a6f3744d
Source dataset
uspto-grants-1989_08
Patent number
US04861799

Reaction notes

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