Sodium Azide → HCID 178527567, compound

HRID 2248134Notes

Reaction equation

HRID 2248134 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]#[N:22])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].C([NH+](CC)CC)C.[N-:31]=[N+:32]=[N-:33].[Na+]>CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]3[NH:33][N:32]=[N:31][N:22]=3)=[CH:18][CH:19]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 12698378Triethylazanium chlorideHCID 19388087HCID 19388087, compound

Product 1

HCID 178527567HCID 178527567, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4.62 g. (13.8 mMol) 4-[2-(4-chlorobenzenesulphonamido)-ethyl]-phenylacetonitrile, 2.94 g. (21.3 mMol) triethylammonium chloride and 2.77 g. (42.6 mMol) sodium azide in 150 ml. 1-methylpyrrolidone are heated to 150° C. for 6 hours. The 1-methylpyrrolidone is subsequently distilled off in a high vacuum at 80° to 90° C., the residue is dissolved in dilute aqueous sodium hydroxide solution and extracted three times with ethyl acetate. The aqueous phase is acidified with hydrochloric acid, also extracted three times with ethyl acetate, the extracts are dried over anhydrous sodium sulphate and, after treating with active charcoal, evaporated to dryness. The residue is taken up in an aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate and acidified, the product thereby crystallising out. There is obtained 1.5 g. (29% of theory) of the title compound in the form of colourless crystals; m.p. 168°-169° C.

Workup

  1. distillationThe 1-methylpyrrolidone is subsequently distilled off in a high vacuum at 80° to 90° C.
  2. dissolutionthe residue is dissolved in dilute aqueous sodium hydroxide solution
  3. extractionextracted three times with ethyl acetate
  4. extractionalso extracted three times with ethyl acetate
  5. dry with materialthe extracts are dried over anhydrous sodium sulphate
  6. additionafter treating with active charcoal
  7. customevaporated to dryness
  8. extractionextracted with ethyl acetate
  9. customthe product thereby crystallising out
  10. customThere is obtained 1.5 g

Sources & evidence

ORD record
ord-79ad7852ee894a5e8881e5b5519f132e
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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