Hydrochloric Acid → HCID 19776263, compound

HRID 1612612Notes

Reaction equation

HRID 1612612 reaction equation
[C:1]([NH:18][C:19]1[C:20](=[O:26])[CH:21]=[CH:22][C:23](=[O:25])[CH:24]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[ClH:27]>C(OCC)(=O)C>[C:1]([NH:18][C:19]1[C:20](=[O:26])[CH:21]=[C:22]([Cl:27])[C:23](=[O:25])[CH:24]=1)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15342880HCID 15342880, compound

Product 1

HCID 19776263HCID 19776263, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 100 g of 2-palmitoylamino-1,4-benzoquinone were added 500 ml of ethyl acetate was stirring. The system was then allowed to undergo reaction at room temperature with hydrogen chloride gas blown thereinto for 2 hours. After completion of the reaction, the reaction system was washed with 1,000 ml of iced water. 50 ml of concentrated nitric acid was then added to the system which was then allowed to undergo reaction at room temperature for 30 minutes. After completion of the reaction, the reaction system was washed with 500 ml of water and then with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine. To the resulting ethyl acetate solution was added 1,500 ml of acetonitrile. The reaction system was then cooled for crystallization. The resulting crystal was filtered off, and then dried to obtain 70 g of 2-palmitoylamino-5-chloro-1,4-benzoquinone. (Yield: 64%)

Workup

  1. customAfter completion of the reaction
  2. washthe reaction system was washed with 1,000 ml of iced water
  3. addition50 ml of concentrated nitric acid was then added to the system which
  4. customreaction at room temperature for 30 minutes
  5. customAfter completion of the reaction
  6. washthe reaction system was washed with 500 ml of water
  7. additionTo the resulting ethyl acetate solution was added 1,500 ml of acetonitrile
  8. temperatureThe reaction system was then cooled for crystallization
  9. filtrationThe resulting crystal was filtered off
  10. customdried

Sources & evidence

ORD record
ord-6cb4581620f14df8ae8653703b32b489
Source dataset
uspto-grants-1993_03
Patent number
US05190852

Reaction notes

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