Hydrochloric Acid → HCID 816703, compound

HRID 257133Notes

Reaction equation

HRID 257133 reaction equation
[Mg].[CH3:2]I.CN(OC)[C:6]([C:8]1[C:16]2[S:15][N:14]=[N:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:7].Cl>C(OCC)C.BrBr.O1CCCC1>[C:6]([C:8]1[C:16]2[S:15][N:14]=[N:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)(=[O:7])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 20096436HCID 20096436, compound

Product 1

HCID 816703HCID 816703, compound

Reagents, catalysts & solvents 3

HCID 24408BromineCatalystHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

0.59 g of magnesium turnings in 3 ml of diethyl ether are activated with 1 drop of bromine, and a solution of 1.5 ml of methyl iodide in 5.5 ml of diethyl ether is added dropwise with stirring. When the exothermic reaction has subsided, the mixture is heated and kept for a further 1.5 hours at bath temperature 55° C. The resulting solution is added dropwise under a nitrogen atmosphere and with stirring at -10° C. to the initially introduced solution of 4.9 g of N-methyl-N-methoxybenzo-1,2,3-thiadiazole-7-carboxamide in 150 ml of absolute tetrahydrofuran. After stirring has been continued for 1 hour at -10° C., the mixture is heated and refluxed at bath temperature 75° C. for 6 hours. The reaction mixture is then cooled, poured into ice-water, acidified with 2N hydrochloric acid and extracted several times using ethyl acetate. The extracts are washed with water, dried over sodium sulfate and evaporated. The residue is purified on silica gel (CHCl3), giving the title compound of m.p. 126°-127° C.

Workup

  1. customWhen the exothermic reaction
  2. temperaturethe mixture is heated
  3. customtemperature 55° C
  4. additionThe resulting solution is added dropwise under a nitrogen atmosphere
  5. stirringAfter stirring
  6. waithas been continued for 1 hour at -10° C.
  7. temperaturethe mixture is heated
  8. temperatureThe reaction mixture is then cooled
  9. extractionextracted several times
  10. washThe extracts are washed with water
  11. dry with materialdried over sodium sulfate
  12. customevaporated
  13. customThe residue is purified on silica gel (CHCl3)

Sources & evidence

ORD record
ord-96c7aa046a0f4c56bc457b8893d41f6f
Source dataset
uspto-grants-1993_11
Patent number
US05260423

Reaction notes

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