1-Butanol → HCID 178437930, compound

HRID 1416416Notes

Reaction equation

HRID 1416416 reaction equation
C(O)CCC.[N-:6]=[N+:7]=[N-:8].[Na+].[CH2:10]([C:12]1[S:16][C:15](=[NH:17])[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]#[N:32])=[CH:21][CH:20]=2)[N:13]=1)[CH3:11].S(=O)(=O)(O)O>[Cl-].[Zn+2].[Cl-].C(Cl)(Cl)Cl>[CH2:10]([C:12]1[S:16][C:15](=[NH:17])[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[NH:32][N:8]=[N:7][N:6]=3)=[CH:21][CH:20]=2)[N:13]=1)[CH3:11]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 15859426HCID 15859426, compound

Product 1

HCID 178437930HCID 178437930, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
115 °C

Procedure

In a 500-ml glass-made reactor equipped with a thermometer and a reflux condenser, 200 ml of n-butanol, 37.5 g of zinc chloride and 50.7 g of sodium azide were charged, followed by stirring for 30 minutes. To the reactor, 50 g of 5-ethyl-2-imino-3-(2'-cyanobiphenyl-4-yl)methyl-1,3,4-thiadiazoline were charged further, followed by heating the internal temperature to 110 to 120° C. at which the reaction was effected for 20 hours. After the completion of the reaction, the reaction mixture was cooled. After the internal temperature decreased to 100° C. or lower, adequate amounts of chloroform and 10% sulfuric acid were added to the reaction mixture, followed by stirring for 30 to 60 minutes. The reaction mixture was cooled and then separated. To the organic layer, a 5% aqueous solution of sodium hydroxide was added. The resulting mixture was stirred for several hours, followed by separation into layers. The aqueous layer was adjusted to pH 7 with 3N hydrochloric acid. The white crystals so precipitated were collected by filtration. The crude crystals so obtained were washed with chloroform under heating and then cooled to room temperature. After cooling to room temperature, the reaction mixture was collected by filtration and dried, whereby about 44.8 g of the title compound was obtained.

Workup

  1. additionwere charged
  2. waitwas effected for 20 hours
  3. customAfter the completion of the reaction
  4. temperaturethe reaction mixture was cooled
  5. customdecreased to 100° C.
  6. stirringby stirring for 30 to 60 minutes
  7. temperatureThe reaction mixture was cooled
  8. customseparated
  9. additionTo the organic layer, a 5% aqueous solution of sodium hydroxide was added
  10. stirringThe resulting mixture was stirred for several hours
  11. customfollowed by separation into layers
  12. customThe white crystals so precipitated
  13. filtrationwere collected by filtration
  14. customThe crude crystals so obtained
  15. washwere washed with chloroform
  16. temperatureunder heating
  17. temperaturecooled to room temperature
  18. temperatureAfter cooling to room temperature
  19. filtrationthe reaction mixture was collected by filtration
  20. customdried

Sources & evidence

ORD record
ord-0673c82a484d4dd48e9bd02618f70f60
Source dataset
uspto-grants-1999_06
Patent number
US05912353

Reaction notes

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