Chloroform → HCID 178527126, compound

HRID 1447565Notes

Reaction equation

HRID 1447565 reaction equation
Cl.N[C:3]1[CH:4]=[CH:5][C:6]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[S:8](=[O:16])(=[O:15])[C:7]=2[CH:17]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+:23].[CH:24](Cl)(Cl)Cl>CN(C)C=O.O>[NH:23]1[C:24]([C:3]2[CH:4]=[CH:5][C:6]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[S:8](=[O:16])(=[O:15])[C:7]=3[CH:17]=2)=[N:20][N:19]=[N:18]1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20384163HCID 20384163, compound

Product 1

HCID 178527126HCID 178527126, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-Aminodibenzothiophene-5,5-dioxide hydrochloride (11.80 g) was diazotised and converted to the crude nitrile as described in Example 24. The crude material was dissolved in chloroform and passed down a column of silica gel (500 g), eluting with chloroform. Evaporation of the solvent gave a mixture of amine and nitrile which was dissolved in dimethyl formamide (30 ml) and treated with sodium azide (1.3 g) and ammonium chloride (1.1 g). After heating on a steam bath for 6 hrs., the solution was diluted with water. The solid precipitate was filtered off and treated with aqueous sodium hydroxide solution (10 ml; 2.5%) at 80° C., filtered, and the filtrate acidified with hydrochloric acid. The product was filtered off, recrystallised from acetic acid and dried at 155° C./15 mm. Hg. m.p. 275° C. (decomposed).

Workup

  1. washeluting with chloroform
  2. customEvaporation of the solvent
  3. customgave
  4. temperatureAfter heating on a steam bath for 6 hrs
  5. filtrationThe solid precipitate was filtered off
  6. additiontreated with aqueous sodium hydroxide solution (10 ml; 2.5%) at 80° C.
  7. filtrationfiltered
  8. filtrationThe product was filtered off
  9. customrecrystallised from acetic acid
  10. customdried at 155° C./15 mm. Hg

Sources & evidence

ORD record
ord-2bf84a62459b4c57bf75d24ae6d95471
Source dataset
uspto-grants-1979_12
Patent number
US04177257

Reaction notes

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