Water → HCID 178508296, compound

HRID 2288622Notes

Reaction equation

HRID 2288622 reaction equation
CN1CCN(C)C1=O.[C:9]([NH:12][NH2:13])([NH2:11])=[NH:10].Cl.[N:15]1([CH2:22][C:23]2[S:27][C:26]([C:28](Cl)=O)=[CH:25][CH:24]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.O>CCCCCC>[NH2:10][C:9]1[NH:12][N:13]=[C:28]([C:26]2[S:27][C:23]([CH2:22][N:15]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:24][CH:25]=2)[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 18699923HCID 18699923, compoundHCID 178418668HCID 178418668, compound

Product 1

HCID 178508296HCID 178508296, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

500 ml of 1,3-dimethyl-2-imidazolidinone and 18.0 g (163.2 mM) of aminoguanidine hydrochloride were added to 24.0 g (81.6 mM) of 5-(hexahydro-1H-azepin-1-yl)methyl-2-thiophenecarbonyl chloride, and the mixture was stirred at room temperature for 1 hour. Then, 16.3 g (60% oil, 408 mM) was added and the mixture was stirred overnight at 130° C. The reaction solution was cooled to room temperature, 50 ml of water and 500 ml of n-hexane were added to effect separation of layers. To the resulting lower layer was added 1,000 ml of saturated brine, and then the mixture was extracted seven times with 500 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, concentrated under a reduced pressure, and 1,000 ml of acetonitrile was added. With ice-cooling, 150 ml of 4 N hydrochloric acid/ethyl acetate was added, and the thus precipitated crystals were collected by filtration. The resulting crystals were added to 200 ml of 1 N sodium hydroxide, extracted three times with 200 ml of ethyl acetate, dried over anhydrous sodium sulfate and then concentrated to 1/10 volume under a reduced pressure. The thus precipitated crystals were collected by filtration to give 10.4 g (51% in yield) of the title compound.

Workup

  1. stirringthe mixture was stirred overnight at 130° C
  2. temperatureThe reaction solution was cooled to room temperature
  3. customseparation of layers
  4. additionTo the resulting lower layer was added 1,000 ml of saturated brine
  5. extractionthe mixture was extracted seven times with 500 ml of ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under a reduced pressure, and 1,000 ml of acetonitrile
  8. additionwas added
  9. temperatureWith ice-cooling
  10. addition150 ml of 4 N hydrochloric acid/ethyl acetate was added
  11. filtrationthe thus precipitated crystals were collected by filtration
  12. additionThe resulting crystals were added to 200 ml of 1 N sodium hydroxide
  13. extractionextracted three times with 200 ml of ethyl acetate
  14. dry with materialdried over anhydrous sodium sulfate
  15. concentrationconcentrated to 1/10 volume under a reduced pressure
  16. filtrationThe thus precipitated crystals were collected by filtration
  17. customto give

Sources & evidence

ORD record
ord-cf0070b0370f407c90a19b9bc3bceb8e
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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