Water → HCID 21195264, compound

HRID 1067931Notes

Reaction equation

HRID 1067931 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=[O:4].[NH:13]1[CH:17]=[N:16][N:15]=[N:14]1.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:14]1[N:15]=[N:16][CH:17]=[N:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 202502,2',4'-TrichloroacetophenoneHCID 178418441HCID 178418441, compound

Product 1

HCID 21195264HCID 21195264, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 15.9 g (71 mmol) of 2,2′,4′-trichloroacetophenone in 100 ml of methylene chloride was slowly added dropwise while cooling with ice to a solution of 4.98 g (71 mmol) of tetrazole and 14.4 g (142 mmol) of triethylamine in 100 ml of methylene chloride and heated under reflux for 16 hours. The reaction mixture was added to 100 ml of water and extracted three times with 100 ml of methylene chloride each time. The combined organic phases were dried over magnesium sulphate and concentrated in a vacuum. The crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:1). There were obtained 4.75 g (26%) of 1-(2,4-dichloro)-2-tetrazol-1-yl-ethanone and 7.80 g (43%) of 1-(2,4-dichlorophenyl)-2-tetrazol-2-yl-ethanone.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. extractionextracted three times with 100 ml of methylene chloride each time
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated in a vacuum
  6. customThe crude product was purified by column chromatography on silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-62153f96cab54507a512e7d810826277
Source dataset
uspto-grants-2001_06
Patent number
US06248901B1

Reaction notes

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