Hydrochloric Acid → HCID 21547382, compound

HRID 1605699Notes

Reaction equation

HRID 1605699 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[N:7]=[CH:6][N:5]=1)[CH3:2].[Al].[C:21](OC(=O)C)(=[O:23])[CH3:22].[ClH:28]>C(OCC)(=O)C.O.C(OCC)C>[ClH:28].[CH2:1]([N:3]([CH2:18][CH3:19])[C:4]1[CH:9]=[C:8]([C:10]2[O:11][C:12]([NH:15][C:21](=[O:23])[CH3:22])=[CH:13][CH:14]=2)[N:7]=[CH:6][N:5]=1)[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 5359268AluminumHCID 21547317HCID 21547317, compound

Product 1

HCID 21547382HCID 21547382, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2.62 g. (0.01 mole) of 4-diethylamino-6-(5-nitro-2-furyl)pyrimidine and aluminum amalgam, prepared from 4.0 g. of aluminum turnings, in 60 ml. of diethyl ether is added 4 ml. of water. Acetic anhydride (2.0 g.; 0.02 mole) is added dropwise during the ensuing reaction which is maintained by heating the reaction vessel in a warm water bath. The ether is filtered and the filtrate dried over sodium sulfate. Removal of the solvent under reduced pressure provides the crude product. The residue is dissolved in ethyl acetate and treated with gaseous hydrogen chloride until a precipitate no longer forms. The resulting hydrochloride salt is further purified by several recrystallizations form methanol/hexane.

Workup

  1. additionTo a mixture of 2.62 g
  2. temperatureis maintained
  3. temperatureby heating the reaction vessel in a warm water bath
  4. filtrationThe ether is filtered
  5. dry with materialthe filtrate dried over sodium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. customprovides the crude product
  8. customThe resulting hydrochloride salt is further purified by several recrystallizations
  9. customform methanol/hexane

Sources & evidence

ORD record
ord-d1a7eed58b8d4cc98377b5252a9c50ed
Source dataset
uspto-grants-1976_04
Patent number
US03950525

Reaction notes

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