Dimethylformamide → HCID 21843588, compound

HRID 1941300Notes

Reaction equation

HRID 1941300 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, starting with pure methylene chloride with increasing methanol content, affords first 2-[1-(4-cyano-phenyl)-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-7b8e4d2aa19d4c92aee922907c582055
Source dataset
uspto-grants-1997_12
Patent number
US05703109

Reaction notes

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