Phosgeniminium chloride → HCID 57600200, compound

HRID 1787788Notes

Reaction equation

HRID 1787788 reaction equation
[Cl-].Cl[C:3](Cl)=[N+:4]([CH3:6])[CH3:5].[CH2:8]([N:13]1[C:21]2[N:20]=[CH:19][NH:18][C:17]=2[C:16](=[O:22])[NH:15]/[C:14]/1=[N:23]/[NH2:24])[CH2:9][CH2:10][CH2:11][CH3:12]>C(Cl)Cl>[CH3:5][N:4]([CH3:6])[C:3]1[N:15]2[C:16](=[O:22])[C:17]3[NH:18][CH:19]=[N:20][C:21]=3[N:13]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:14]2=[N:23][N:24]=1

Participants

4

Reactant 2

HCID 2723945Phosgeniminium chlorideHCID 178446165HCID 178446165, compound

Product 1

HCID 57600200HCID 57600200, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methylene chloride (10 mL) was added [B] N-(dichloromethylene)-N-methylmethanaminium chloride (0.21 g, 1.3 mmol). After stirring for 5 mins, (2Z)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.10 g, 0.42 mmol) was added, and the mixture was stirred at rt for 5 hrs. LCMS analysis showed product as a major peak was formed. 1N NaoH was carefully added to neutralize the acid, and the mixture was extracted with methylene chloride three times. The combined organic layers were dried by MgSO4, filtered and concentrated in vacuo to yield the desired product (84 mg, 69%). LCMS calculated for C13H20N7O(M+H): 290.2; found 290.1.

Workup

  1. stirringthe mixture was stirred at rt for 5 hrs
  2. customwas formed
  3. addition1N NaoH was carefully added
  4. extractionthe mixture was extracted with methylene chloride three times
  5. dry with materialThe combined organic layers were dried by MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc02c5609ee940d09db25e8d72d847db
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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