p-Aminoacetophenone → HCID 20525904, compound

HRID 1105700Notes

Reaction equation

HRID 1105700 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.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][CH2:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:27]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1)[CH2:26][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][CH3:12]

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 1-bromohexadecane (198 g.) in dry hexamethyl phosphoramide (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 the product of the Example.

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
  8. customprovides the product of the Example

Sources & evidence

ORD record
ord-b63c8438dab241b7af2868fbd120736b
Source dataset
uspto-grants-1982_01
Patent number
US04309553

Reaction notes

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