Dimethylformamide → HCID 178434829, compound

HRID 233331Notes

Reaction equation

HRID 233331 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]#[N:25])=[CH:18][CH:17]=1.[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]2[NH:28][N:27]=[N:26][N:25]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 109696383-[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionitrile

Product 1

HCID 178434829HCID 178434829, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionitrile (0.7 g), sodium azide (0.411 g), ammonium chloride (0.337 g) and N,N-dimethylformamide (15 ml) was stirred for 24 hours at 120° C. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried, then the solvent was distilled off to leave 5-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]ethyl]tetrazole (0.38 g, 48%), which was recrystallized from ethyl acetate--hexane to give colorless prisms, m.p.143°-144° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. customdried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-a7ffd3e7356647b8a9d1560cf7806985
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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