Dimethylformamide → HCID 178420131, compound

HRID 653110Notes

Reaction equation

HRID 653110 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][CH:10]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:18]=1)#[N:2].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+].CN(C)C=O>O>[C:12]1([C:9]2[C:8]3[CH:18]=[C:4]([CH2:3][C:1]4[NH:21][N:20]=[N:19][N:2]=4)[CH:5]=[CH:6][C:7]=3[O:11][CH:10]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20195529HCID 20195529, compound

Product 1

HCID 178420131HCID 178420131, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.6 g. (0.02 mole) of 5-cyanomethyl-3-phenylbenzofuran, 1.5 g. of sodium azide and 1.2 g. of ammonium chloride in 15 ml. of N,N-dimethylformamide is heated at 110° C. for 20 hours. The reaction mixture is poured into 200 ml. of water and stirred. The mixture is extracted with 50 ml. of chloroform. The extracts are washed with water, then dried over magnesium sulfate. Evaporation provides a residue which is recrystallized from ethyl acetate to provide 3-phenyl-5-(1H-tetrazol-5yl)methylbenzofuran.

Workup

  1. additionA mixture of 4.6 g
  2. additionThe reaction mixture is poured into 200 ml
  3. extractionThe mixture is extracted with 50 ml
  4. washThe extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation
  7. customprovides a residue which
  8. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ac42bcdde7f84cfe969f47d0b3ef0ec6
Source dataset
uspto-grants-1987_06
Patent number
US04675320

Reaction notes

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