p-Aminoacetophenone → HCID 20525904, compound

HRID 2049850Notes

Reaction equation

HRID 2049850 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:26]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 82131-BromohexadecaneHCID 11430Potassium Carbonate

Product 1

HCID 20525904HCID 20525904, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

p-Aminoacetophenone (87.6 g.) is heated with hexadecylbromide (198 g.) in dry hexamethylphosphoramide (300 ml.) containing anhydrous potassium carbonate (90 g.) for 16 hours at 100° C. The solution is cooled to room temperature, filtered to remove solids, and the filtrate is diluted with cold water (20 ml.). The amber solid so obtained is collected and washed with water. Recrystallization from ethanol followed by dichloromethane provides p-hexadecylaminoacetophenone.

Workup

  1. filtrationfiltered
  2. customto remove solids
  3. additionthe filtrate is diluted with cold water (20 ml.)
  4. customThe amber solid so obtained
  5. customis collected
  6. washwashed with water
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-dc86704a25e14ffc81d8e3727983ec0c
Source dataset
uspto-grants-1980_04
Patent number
US04198522

Reaction notes

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