Ethanol → HCID 57927174, compound

HRID 889147Notes

Reaction equation

HRID 889147 reaction equation
O.[NH2:2][NH2:3].I.[CH2:5]([N:12]([CH3:18])[C:13](=[N:16][CH3:17])OC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:19]([OH:21])C>>[CH2:5]([N:12]([CH3:18])[C:13]1[N:16]([CH3:17])[C:19](=[O:21])[NH:2][N:3]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 68676283HCID 68676283, compound

Product 1

HCID 57927174HCID 57927174, compound

Procedure

Hydrazine hydrate (9.41 ml) was added to a mixture of 1-benzyl-1,2,3-trimethyl-isourea hydroiodide (CAS 56043-41-5) (65.2 g) and ethanol (400 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, pyridine (300 ml) was added to the residue, and ethyl chloroformate (20.4 ml) was added dropwise while stirring on ice. After heating to reflux for 1 hour and 30 minutes, the reaction mixture was concentrated under reduced pressure. After then adding N,N-dimethylformamide (452 ml) to the residue, the mixture was stirred at 150° C. for 17 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained solid was recrystallized from diethyl ether-n-heptane to obtain the title compound (17.2 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, pyridine (300 ml)
  2. additionwas added to the residue, and ethyl chloroformate (20.4 ml)
  3. additionwas added dropwise
  4. stirringwhile stirring on ice
  5. temperatureAfter heating
  6. temperatureto reflux for 1 hour and 30 minutes
  7. concentrationthe reaction mixture was concentrated under reduced pressure
  8. stirringAfter then adding N,N-dimethylformamide (452 ml) to the residue, the mixture was stirred at 150° C. for 17 hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  10. additionwas added to the residue
  11. filtrationthe mixture was filtered
  12. concentrationThe filtrate was concentrated under reduced pressure
  13. customthe residue was purified by silica gel column chromatography
  14. customThe obtained solid was recrystallized from diethyl ether-n-heptane

Sources & evidence

ORD record
ord-13a3b19c53e34121be24febcd1295e63
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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