Acetyl chloride → HCID 14555273, compound

HRID 1723483Notes

Reaction equation

HRID 1723483 reaction equation
[CH2:1]([NH:8][C:9](=[O:26])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([OH:25])=[O:24])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](Cl)(=O)C>CO>[CH2:1]([NH:8][C:9](=[O:26])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([O:25][CH3:27])=[O:24])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 14555270HCID 14555270, compound

Product 1

HCID 14555273HCID 14555273, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

N-Benzyl 2-(3-carboxyphenoxy)nicotinamide (1.00 gram, 2.87 mmol) is slurried in 12 ml of methanol in a 125 ml round bottom flask equipped with magnetic stir bar and nitrogen source and chilled to 0° C. Acetyl chloride (0.57 ml) is added to the flask and the reaction allowed to slowly warm to room temperature. After 18 hours the reaction is quenched by adding 50 ml of 2N sodium hydroxide solution. It is then extracted (2×50 ml) with ethyl acetate, the combined extracts washed with (2×100 ml) 2N sodium hydroxide and dried over anhydrous magnesium sulfate. Filtration and concentration of the extract in vacuo yield a pasty solid which is purified by trituration with diethyl ether to yield 0.38 grams (36.5%) of the title product as a white crystalline solid.

Workup

  1. customequipped with magnetic stir bar
  2. temperatureto slowly warm to room temperature
  3. customAfter 18 hours the reaction is quenched
  4. additionby adding 50 ml of 2N sodium hydroxide solution
  5. extractionIt is then extracted (2×50 ml) with ethyl acetate
  6. washthe combined extracts washed with (2×100 ml) 2N sodium hydroxide
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationFiltration and concentration of the
  9. extractionextract in vacuo
  10. customyield a pasty solid which
  11. customis purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-b800607b12e042208b238b142bea9cba
Source dataset
uspto-grants-1989_08
Patent number
US04861891

Reaction notes

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