Dimethyl Sulfate → HCID 89875225, compound

HRID 1048623Notes

Reaction equation

HRID 1048623 reaction equation
[CH3:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[NH:12][N:11]=[N:10]1.[C:15](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][C:2]1[C:7]([I:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](=[O:14])[N:12]([CH3:15])[N:11]=[N:10]1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 136646184HCID 136646184, compound

Product 1

HCID 89875225HCID 89875225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of the above-mentioned 1-(2-methyl-3-iodophenyl)-1,4-dihydrotetrazole-5-one, potassium carbonate 17.40 g, dimethyl sulfate 5.78 g and N,N-dimethylformamide 150 mL was stirred at 25° C. for one hour. To the reaction mixtures was added aqueous saturated sodium bicarbonate solution and the mixtures were extracted with ethyl acetate. The organic layers were washed with aqueous saturated sodium bicarbonate solution and were dried over anhydrous sodium sulfate. The resulting mixtures were concentrated under reduced pressure to give 1-(2-methyl-3-iodophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Intermediate (PRI-P)”) 8.10 g.

Workup

  1. customTo the reaction mixtures
  2. extractionthe mixtures were extracted with ethyl acetate
  3. washThe organic layers were washed with aqueous saturated sodium bicarbonate solution
  4. dry with materialwere dried over anhydrous sodium sulfate
  5. concentrationThe resulting mixtures were concentrated under reduced pressure

Sources & evidence

ORD record
ord-6591d9807b084d069a922e56e41c7bab
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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