Acetaminophen → HCID 50914086, compound

HRID 728528Notes

Reaction equation

HRID 728528 reaction equation
[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:34])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:12][C:11]=2[N+:35]([O-:37])=[O:36])[C:7](=[O:38])[C:6]=1[CH2:39]Cl)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C([NH:52][C:53]1[CH:58]=[CH:57][C:56]([OH:59])=[CH:55][CH:54]=1)(=O)C>CC(C)=O>[C:1]([C:5]1[O:9][N:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:34])[NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:12][C:11]=2[N+:35]([O-:37])=[O:36])[C:7](=[O:38])[C:6]=1[CH2:39][O:59][C:56]1[CH:57]=[CH:58][C:53]([NH2:52])=[CH:54][CH:55]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1983AcetaminophenHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14324465HCID 14324465, compound

Product 1

HCID 50914086HCID 50914086, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5.8 g of 5-t-butyl-4-chloromethyl-2-(4-n-hexadecylcarbamoyl-2-nitrophenyl)-4-isooxazolin-3-one and 1.4 g of potassium carbonate were mixed with 40 ml of acetone, and thereto were added 0.4 g of sodium iodide and 0.4 ml of polyethylene glycol. Thereto, 1.7 g of 4-acetylaminophenol was further added, and the resulting mixture was heated under reflux for 5 hours. After the completion of the reaction, crystals were precipitated by addition of diluted hydrochloric acid, and then filtered off. To the crystals taken out were added 40 ml of ethanol and 20 ml of concentrated hydrochloric acid, and the mixture was heated under reflux for 4 hours. After cooling, crystals separated out on stirring. They were filtered off, and washed successively with acetonitrile and acetone. Yield: 5.5 g, Percent yield: 79.4%, Melting point: 220° C. or higher.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customAfter the completion of the reaction, crystals
  4. customwere precipitated by addition of diluted hydrochloric acid
  5. filtrationfiltered off
  6. additionTo the crystals taken out were added 40 ml of ethanol and 20 ml of concentrated hydrochloric acid
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 4 hours
  9. temperatureAfter cooling
  10. customcrystals separated out
  11. filtrationThey were filtered off
  12. washwashed successively with acetonitrile and acetone

Sources & evidence

ORD record
ord-8f9a6f0420bb48d0b39a12d6898b7c79
Source dataset
uspto-grants-1991_09
Patent number
US05049477

Reaction notes

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