Acetic Acid → 1-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]phenyl}-1H-tetrazole

HRID 1930523Notes

Reaction equation

HRID 1930523 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][C:11]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[CH2:10]2)[CH:6]=[CH:5][C:3]=1[NH2:4].C(OCC)(OCC)OCC.[N-:36]=[N+:37]=[N-:38].[Na+].[C:40](O)(=O)C>O>[Br:1][C:2]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][C:11]([C:18]3[CH:19]=[C:20]([Cl:25])[CH:21]=[C:22]([Cl:24])[CH:23]=3)([C:14]([F:15])([F:16])[F:17])[CH2:10]2)[CH:6]=[CH:5][C:3]=1[N:4]1[CH:40]=[N:38][N:37]=[N:36]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 582188902-Bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]aniline

Product 1

HCID 582188931-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]phenyl}-1H-tetrazoleYield 77.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To the mixture of 2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]aniline (0.60 g), triethyl orthoformate (0.98 g) and sodium azide (0.38 g) was added acetic acid (1.1 g), and the mixture was then heated with stirring at 100° C. for 4 hours. The mixture was cooled to room temperature and then poured into water, which was then extracted twice with ethyl acetate. The organic layer was combined, which was then washed with water and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the solvent was distilled away under the reduced pressure, and the residue was then purified by silica gel chromatography to yield 1-{2-bromo-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]phenyl}-1H-tetrazole (0.52 g). m.p. 193-194° C.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionwas then extracted twice with ethyl acetate
  4. washwhich was then washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter the drying agent was filtered off
  7. distillationthe solvent was distilled away under the reduced pressure
  8. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-8d59b51b45b046799c73227056a633c2
Source dataset
uspto-grants-2012_05
Patent number
US08188122B2

Reaction notes

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