Dichloromethane → 5-Acetonylthio-1,4-dimethyltetrazolium chloride

HRID 728032Notes

Reaction equation

HRID 728032 reaction equation
[CH2:1]([S:5][C:6]1[N:10]([CH3:11])[N:9]=[N:8][N:7]=1)[C:2]([CH3:4])=[O:3].F[C:13](F)(F)S(OC)(=O)=O.C(Cl)[Cl:22]>CO>[Cl-:22].[CH2:1]([S:5][C:6]1[N:10]([CH3:11])[N:9]=[N:8][N+:7]=1[CH3:13])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 9526Methyl triflateHCID 30619772-Propanone, 1-((1-methyl-1H-tetrazol-5-yl)thio)-

Product 1

HCID 150071015-Acetonylthio-1,4-dimethyltetrazolium chloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The 5-acetonylthio-1-methyltetrazole, prepared as above described, was dissolved in 20 ml of methylene chloride and to the resulting solution was added 0.617 gram (0.0055 mol) of methyl trifluoromethanesulfonate and the mixture allowed to stand overnight at room temperature. Thereafter, the solvent was vaporized off and an oily residue obtained. The latter was dissolved in aqueous methanol and the methanol solution passed over a Dowex-1 (Cl-) ion exchange column. The eluate from the column was evaporated to obtain a waxy material which was triturated with hexane to obtain a waxy solid which after drying in high vacuum amounted to 0.80 gram of 5-acetonylthio-1,4-dimethyltetrazolium chloride, m.p. 102°-104° C.

Workup

  1. customan oily residue obtained
  2. customThe eluate from the column was evaporated
  3. customto obtain a waxy material which
  4. customwas triturated with hexane
  5. customto obtain a waxy solid which
  6. customafter drying in high vacuum

Sources & evidence

ORD record
ord-ebf58799f27d43c88fd0ee0127a3dc64
Source dataset
uspto-grants-1991_09
Patent number
US05047416

Reaction notes

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