Hydrochloric Acid → HCID 136646183, compound

HRID 1048633Notes

Reaction equation

HRID 1048633 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]=[C:19]=[O:20])[C:13]=1[CH3:21])[CH3:10].N([O-])=O.[Na+].Cl>O.CN(C)C=O>[CH3:21][C:13]1[C:12]([O:11][CH2:9][CH3:10])=[CH:17][CH:16]=[CH:15][C:14]=1[N:18]1[C:19](=[O:20])[NH:7][N:6]=[N:5]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 23668193Sodium NitriteHCID 89875585HCID 89875585, compound

Product 1

HCID 136646183HCID 136646183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Under ice-cooling, to a mixture of N,N-dimethylformamide 350 mL and anhydrous aluminum chloride 33.6 g was added sodium azide 15 g, and the resulting mixtures were stirred for one hour. Thereto was thereafter added 1-ethoxy-3-isocyanato-2-methylbenzene described in Reference Preparation example 2737.2 g and the resulting mixtures were heated to 75° C. and were stirred for five hours. The mixtures were cooled and under ice-cooling, to the reaction mixtures was added ice water 100 mL, followed by addition of a mixture of sodium nitrite 23 g and water 150 mL, and the mixtures were acidified with concentrated hydrochloric acid to pH about 4. 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)-1,4-dihydrotetrazole-5-one 39.0 g.

Workup

  1. stirringwere stirred for five hours
  2. temperatureThe mixtures were cooled and under ice-
  3. temperaturecooling, to the reaction mixtures
  4. extractionThe mixtures were extracted with ethyl acetate
  5. washthe organic layers were washed with water and saturated saline
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. concentrationwere then concentrated under reduced pressure

Sources & evidence

ORD record
ord-c0079cdedc444569b26230c9ea02b7aa
Source dataset
uspto-grants-2016_07
Patent number
US09380782B2

Reaction notes

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