HCID 13687979, compound → HCID 178523916, compound

HRID 1493334Notes

Reaction equation

HRID 1493334 reaction equation
[C:1]([NH:9][C:10](=[N:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)OC1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][NH2:37])[N:31]=[CH:30]1>C(#N)C>[C:1]([NH:9][C:10]([NH:37][CH2:36][CH2:35][CH2:34][C:32]1[N:31]=[CH:30][NH:29][CH:33]=1)=[N:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13687979HCID 13687979, compoundHCID 178510931HCID 178510931, compound

Product 1

HCID 178523916HCID 178523916, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The previously obtained solution of 6.1 mmol of N-benzoyl-N'-(3-phenoxypropyl)-O-phenyl-isourea is concentrated by evaporation under vacuum and the residue is dissolved in acetonitrile and then heated under reflux for 3 hours after the addition of 0.8 g (6.4 mmol) of 3-(imidazol-4-yl)-propylamine. The reaction mixture obtained is then concentrated by evaporation under vacuum, the residue is taken up with dilute hydrochloric acid and the aqueous solution is extracted three times with ether. After alkalisation with sodium hydroxide solution, the reaction product is extracted from the aqueous phase with methylene chloride, the extract obtained is concentrated by evaporation, and the reaction product is crystallised from the concentrated extract by means of ethyl acetate. 0.95 g (38%) of colourless solid melting at 149° C. after recrystallisation from ethanol/water is obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customThe reaction mixture obtained
  4. concentrationis then concentrated by evaporation under vacuum
  5. extractionthe aqueous solution is extracted three times with ether
  6. extractionAfter alkalisation with sodium hydroxide solution, the reaction product is extracted from the aqueous phase with methylene chloride
  7. customthe extract obtained
  8. concentrationis concentrated by evaporation
  9. customthe reaction product is crystallised from the concentrated
  10. extractionextract by means of ethyl acetate
  11. custom0.95 g (38%) of colourless solid melting at 149° C. after recrystallisation from ethanol/water
  12. customis obtained

Sources & evidence

ORD record
ord-bbb8396e31244818a2cf108c7879e5b8
Source dataset
uspto-grants-1991_06
Patent number
US05021431

Reaction notes

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