Acetic Anhydride → HCID 21535060, compound

HRID 1657635Notes

Reaction equation

HRID 1657635 reaction equation
[CH3:1][C:2]1[CH:33]=[C:32]([NH:34][C:35](=[O:37])[CH3:36])[CH:31]=[CH:30][C:3]=1[O:4][CH2:5][CH:6]([OH:29])[CH2:7][N:8]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][CH:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:38](OC(=O)C)(=[O:40])[CH3:39].[OH-].[Na+]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:33]=[C:32]([NH:34][C:35](=[O:37])[CH3:36])[CH:31]=[CH:30][C:3]=1[O:4][CH2:5][CH:6]([O:29][C:38](=[O:40])[CH3:39])[CH2:7][N:8]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][CH:20]=1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 21535048HCID 21535048, compound

Product 1

HCID 21535060HCID 21535060, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Two grams of 1-(2-methyl-4-acetamidophenoxy)-3-{N-[2-(4-acetamidophenoxy)ethyl]-N-benzylamino}propan-2-ol are added to 20 ml. of anhydrous pyridine, followed by the immediate addition of 8.0 g. of acetic anhydride to the mixture with stirring. The resulting solution is then refluxed for a period of five minutes, cooled and subsequently poured into 50 ml. of ice water. The latter aqueous soltuion is then basified with 2N aqueous sodium hydroxide solution and extracted with chloroform, and the chloroform extract is thereafter washed with water and dried over anhydrous sodium sulfate prior to concentration in vacuo. The crude product obtained in this manner is then recrystallized from ethanol to afford pure 1-(2-methyl-4-acetamidophenoxy)-3-{N-[2-(4-acetamidophenoxy)ethyl]-N-benzylamino}-2-acetoxypropane. On subsequent treatment with hydrogen in the presence of palladium-on-carbon, the latter compound then gave 1-(2-methyl-4-acetamidophenoxy)-3-[2-(4-acetamidophenoxy)ethylamino]-2-acetoxypropane.

Workup

  1. temperatureThe resulting solution is then refluxed for a period of five minutes
  2. temperaturecooled
  3. additionsubsequently poured into 50 ml
  4. extractionextracted with chloroform
  5. extractionthe chloroform extract
  6. washis thereafter washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationto concentration in vacuo
  9. customThe crude product obtained in this manner
  10. customis then recrystallized from ethanol

Sources & evidence

ORD record
ord-583afde174264f5ebc83bc754b2ff5ab
Source dataset
uspto-grants-1976_06
Patent number
US03961072

Reaction notes

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