Methanesulfonyl chloride → 5-(2,4-Dinitrophenylthio)-1-(2-methanesulfonamidoethyl)tetrazole

HRID 866879Notes

Reaction equation

HRID 866879 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9]([S:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])=[N:8][N:7]=[N:6]1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[N+:20]([C:12]1[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:11]=1[S:10][C:9]1[N:5]([CH2:4][CH2:3][NH:2][S:24]([CH3:23])(=[O:26])=[O:25])[N:6]=[N:7][N:8]=1)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 203828111-(2-Aminoethyl)-5-(2,4-dinitrophenylthio)tetrazole hydrochloride

Product 1

HCID 203186985-(2,4-Dinitrophenylthio)-1-(2-methanesulfonamidoethyl)tetrazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 4.9 g (14.1 mmol) of 1-(2-aminoethyl)-5-(2,4-dinitrophenylthio)tetrazole hydrochloride in 100 ml of pyridine was added 1.5 ml (2.2 g, 19.2 mmol) of methanesulfonyl chloride. The mixture was stirred for 1.5 hours, then an additional 0.5 ml of methanesulfonyl chloride was added and the mixture was stirred another hour. The pyridine was removed by evaporation and the residue was dissolved in a small volume of dimethylformamide. Water was added to the solution and the resulting precipitate was collected by filtration, washed with watr and air dried. The precipitate was dissolved in a minimum amount of dimethylformamide and the solution was diluted with ethyl acetate and treated with Darco G-60. The mixture was filtered and evaporated to dryness to give a syrupy residue which was crystallized from ethyl acetate to give 5-(2,4-dinitrophenylthio)-1-(2-methanesulfonamidoethyl)tetrazole.

Workup

  1. stirringthe mixture was stirred another hour
  2. customThe pyridine was removed by evaporation
  3. dissolutionthe residue was dissolved in a small volume of dimethylformamide
  4. additionWater was added to the solution
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with watr and air
  7. customdried
  8. dissolutionThe precipitate was dissolved in a minimum amount of dimethylformamide
  9. additionthe solution was diluted with ethyl acetate
  10. additiontreated with Darco G-60
  11. filtrationThe mixture was filtered
  12. customevaporated to dryness
  13. customto give a syrupy residue which
  14. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-69ad80dfb7c442f68d85908ba6dba9a9
Source dataset
uspto-grants-1978_07
Patent number
US04101656

Reaction notes

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