Dimethylformamide → HCID 178420130, compound

HRID 653105Notes

Reaction equation

HRID 653105 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][CH:9]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]=2[CH:17]=1)#[N:2].[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+].CN(C)C=O>O>[C:11]1([C:8]2[C:7]3[CH:17]=[C:3]([C:1]4[NH:22][N:21]=[N:20][N:2]=4)[CH:4]=[CH:5][C:6]=3[O:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20195497HCID 20195497, compound

Product 1

HCID 178420130HCID 178420130, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 61.4 g. (0.28 mole) of 5-cyano-3-phenylbenzofuran (described in U.S. Pat. No. 4,067,993, Example 1), 16.5 g. (0.31 mole) of ammonium chloride and 20.2 g. (0.31 mole) of sodium azide in 250 ml. of N,N-dimethylformamide is stirred at 110°-120° C. for 16 hours. The mixture is cooled to about 20° C. and poured into about 1 liter of water. A light brown solid forms which is collected by filtration, washed with water, and then recrystallized from ethanol to provide brown crystals of 3-phenyl-5-(1H-tetrazol-5-yl)benzofuran.

Workup

  1. additionA mixture of 61.4 g
  2. filtrationA light brown solid forms which is collected by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8924be51308f42d8b30606078c06e91f
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

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