Dimethylformamide → HCID 21843588, compound

HRID 1737872Notes

Reaction equation

HRID 1737872 reaction equation
[H-].[Na+].CN(C=O)C.[NH:8]1[CH:12]=[N:11][N:10]=[N:9]1.Cl[CH:14]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1>O>[C:30]([C:27]1[CH:26]=[CH:25][C:24]([CH:14]([N:9]2[N:10]=[N:11][CH:12]=[N:8]2)[CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[CH:29][CH:28]=1)#[N:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 21843579HCID 21843579, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 21843588HCID 21843588, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaH (0.45 g of 55% suspension in mineral oil) is added to anhydrous DMF under nitrogen atmosphere. Tetrazole (1.1 g) is added and the mixture is gently heated for 20 minutes. The mixture is cooled to room temperature and 1-chloro-1-(4-cyanophenyl)3-(4-fluorophenyl)propane (1.53 g) is added. The reaction mixture is then heated for 6 hours. Water is added and the products are extracted into ethyl acetate. After drying and solvent evaporation the products are purified by flash chromatography. Elution, staring with pure methylene chloride with increasing methanol content, affords first 2-[1-(4-cyanophenyl)-3-(4-fluorophenyl)propyl]tetrazole which 1H NMR spectra is as follows:

Workup

  1. temperaturethe mixture is gently heated for 20 minutes
  2. temperatureThe reaction mixture is then heated for 6 hours
  3. extractionthe products are extracted into ethyl acetate
  4. customAfter drying
  5. customsolvent evaporation the products
  6. customare purified by flash chromatography
  7. washElution

Sources & evidence

ORD record
ord-1dc542bbd83044f3b5566e30cfd6f787
Source dataset
uspto-grants-1999_10
Patent number
US05962495

Reaction notes

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