Acetyl chloride → HCID 22612117, compound

HRID 844037Notes

Reaction equation

HRID 844037 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8](=[O:23])[C:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34]>C(Cl)Cl.O>[C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8](=[O:23])[C:9]2[CH:14]=[CH:13][CH:12]=[N:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:24][CH:25]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22612153HCID 22612153, compound

Product 1

HCID 22612117HCID 22612117, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-Amino-benzyl)-2-(4-fluoro-phenoxy)-nicotinamide (0.105 grams, 0.31 mmole) and triethyl amine (0.047 grams, 0.46 mmole) in methylene chloride was cooled to 0° C., and Acetyl chloride (0.029 grams, 0.37 mmole) was added. The mixture was stirred for 10 minutes and then allowed to warm to room temperature for 30 minutes. The mixture was diluted with water and extracted with methylene chloride. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to give a solid . Recrystalization from ethyl acetate/hexane gave a white solid. (0.082 g). M.P. 128-130° C.; Anal. calcd. for C21H18N3O3F: C, 66.48; H, 4.78; N, 11.08. Found: C, 66.14; H, 4.47; N, 11.08.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid
  7. customRecrystalization from ethyl acetate/hexane
  8. customgave a white solid

Sources & evidence

ORD record
ord-6ea72f1ed68e46ac8a9ce93b8350390a
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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