Ammonium Chloride → HCID 178515052, compound

HRID 596974Notes

Reaction equation

HRID 596974 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:17])[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:18]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:17])[C:8]4[C:13]([S:14][C:15]=3[CH:16]=2)=[CH:12][CH:11]=[CH:10][CH:9]=4)=[N:2][N:20]=[N:19]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1039569-Oxo-9H-thioxanthene-3-carbonitrile

Product 1

HCID 178515052HCID 178515052, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-cyanothioxanthone (2.56 g), sodium azide (0.84 g) and ammonium chloride (0.70 g) in dimethylformamide (20 ml) was heated on a steam bath for 5 hrs. The nitrile dissolved after 2 hr., at the same time a precipitate of the product forming. Much solid crystallised out on cooling. The reaction mixture was poured into excess dilute hydrochloric acid, and the yellow precipitate was filtered off and washed with water. It was dissolved in dilute aqueous sodium hydroxide, filtered and reprecipitated with dilute hydrochloric acid. The product was filtered off and dried at 110° C, and then recrystallised from dimethylformamide and dried at 154° C/15mm. Hg, decomposes 290° C.

Workup

  1. temperaturewas heated on a steam bath for 5 hrs
  2. custom, at the same time a precipitate of the product forming
  3. customMuch solid crystallised out
  4. temperatureon cooling
  5. additionThe reaction mixture was poured into excess dilute hydrochloric acid
  6. filtrationthe yellow precipitate was filtered off
  7. washwashed with water
  8. dissolutionIt was dissolved in dilute aqueous sodium hydroxide
  9. filtrationfiltered
  10. customreprecipitated with dilute hydrochloric acid
  11. filtrationThe product was filtered off
  12. customdried at 110° C
  13. customrecrystallised from dimethylformamide
  14. customdried at 154° C/15mm. Hg
  15. customdecomposes 290° C.

Sources & evidence

ORD record
ord-d186bec9b9994d269f2b00423c35eb67
Source dataset
uspto-grants-1977_03
Patent number
US04012499

Reaction notes

Loading…