Acetic Acid → HCID 178478115, compound

HRID 1655355Notes

Reaction equation

HRID 1655355 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1.[N-:18]=[N+:19]=[N-:20].[Na+].C(O)(=O)C>C(O)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]2[NH:20][N:19]=[N:18][N:12]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 33557Sodium Azide2×HCID 3402182HCID 3402182, compound

Product 1

HCID 178478115HCID 178478115, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

To a solution of 5×10-2 mole of 4-(3-chloro benzyloxy) benzonitrile in 20 ml of butanol are added 6.6×10-2 mole of sodium azide and 6.6×10-2 of acetic acid. Then the reaction mixture is heated to reflux for four days. 1 g of sodium azide, 2 g of acetic acid and 10 ml of butanol are added and the medium is again heated for two days at reflux. After concentrating by evaporating the solvent, the residue is taken up in 20 ml of 10% aqueous NaOH. After filtration, the aqueous phase is extracted with ether. By acidification of the alkaline solution using HCl 2N, the expected compound precipitates and is recrystallized in methanol.

Workup

  1. temperatureThen the reaction mixture is heated
  2. temperatureto reflux for four days
  3. temperaturethe medium is again heated for two days
  4. temperatureat reflux
  5. concentrationAfter concentrating
  6. customby evaporating the solvent
  7. filtrationAfter filtration
  8. extractionthe aqueous phase is extracted with ether
  9. customthe expected compound precipitates
  10. customis recrystallized in methanol

Sources & evidence

ORD record
ord-ac7acdd1480f43c9a2a9a811baf5f47a
Source dataset
uspto-grants-1993_10
Patent number
US05250551

Reaction notes

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