Water → HCID 23508388, compound

HRID 1883672Notes

Reaction equation

HRID 1883672 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](OC(=O)C)(=[O:26])[CH3:25].[OH2:31].N1[CH:37]=[CH:36]C=CC=1>>[C:24]([O:21][C:18]1[CH:17]=[CH:16][C:15]([N:14]([C:36](=[O:31])[CH3:37])[CH2:13][C:12]2[CH:22]=[CH:23][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[CH:20][CH:19]=1)(=[O:26])[CH3:25]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 833994HCID 833994, compound

Product 1

HCID 23508388HCID 23508388, compound

Procedure

100 mg of 4-[N-(4-benzyloxybenzyl)amino]phenol was dissolved in 4 ml of pyridine, and 2 ml of acetic anhydride was added thereto, followed by stirring at room temperature for 2 hours. After water was added to the reaction mixture, the product was extracted with ethyl acetate. The organic layer was washed with 5% hydrochloric acid and a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by TLC (using chloroform as the developing solvent) to obtain 114 mg of 4-[N-acetyl-N-(4-benzyloxy-benzyl)amino]phenyl acetate.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with 5% hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe resulting crude product was purified by TLC (

Sources & evidence

ORD record
ord-a825dbf04a0940f9a605e9271d5c1a90
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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