Dimethylformamide → HCID 89875881, compound

HRID 1048634Notes

Reaction equation

HRID 1048634 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[NH:14][N:13]=[N:12]1.[C:17](=O)([O-])[O-].[K+].[K+].CN(C)C=O.S(OC)(OC)(=O)=O>O>[CH3:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 136646183HCID 136646183, compound

Product 1

HCID 89875881HCID 89875881, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, to a mixture of 1-(2-methyl-3-ethoxyphenyl)-1,4-dihydrotetrazole-5-one 39.0 g, potassium carbonate 36.7 g and N,N-dimethylformamide 400 mL was added dimethyl sulfate 44.7 g and the resulting mixtures were raised to room temperature and were stirred for seven hours. Thereto was added water and the mixtures were extracted with ethyl acetate and the organic layers were washed with water and saturated saline, and were dried over anhydrous magnesium sulfate and were then concentrated under reduced pressure. The resulting residues were subjected to a silica gel column chromatography to give 1-(2-methyl-3-ethoxyphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 38.2 g.

Workup

  1. extractionthe mixtures were extracted with ethyl acetate
  2. washthe organic layers were washed with water and saturated saline
  3. dry with materialwere dried over anhydrous magnesium sulfate
  4. concentrationwere then concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d0888b8740646e186ceb30047fdf103
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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