Ethanol → HCID 591251, compound

HRID 461438Notes

Reaction equation

HRID 461438 reaction equation
[CH:1]([C:4]1[CH:13]=[CH:12][C:7](N[N+]([O-])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(O)C.S(=O)(=O)(O)O.[N:22]([O-:24])=[O:23].[Na+]>C(Cl)(Cl)Cl.O>[CH:1]([C:4]1[CH:5]=[C:6]([N+:22]([O-:24])=[O:23])[CH:7]=[CH:12][CH:13]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 54440934HCID 54440934, compound

Product 1

HCID 591251HCID 591251, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

3.56 G. of 4-isopropylnitroaniline is dissolved in 580 ml. of ethanol and stirred. 30.4 Ml. of concentrated sulfuric acid is added dropwise. The reaction mixture is heated to reflux and a solution of 16 g. of sodium nitrite in 25 ml. of water is added dropwise over 5 minutes. Heating is continued for 1 hour and then the reaction mixture is allowed to cool to room temperature. 250 Ml. of water and 1200 ml. of chloroform is added, the layers are separated and the water layer is extracted with an additional 230 ml. of chloroform. The chloroform layers are combined, washed with 250 ml. of water, dried over sodium sulfate and the solvent is removed by distillation through a short vigreau column at atmosphere pressure. The residue is vacuum distilled at from 8.6 to 9.0 mm. of Hg. The fraction taken at 112° to 128° C. is used as is in the next step.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. temperatureHeating
  4. customthe layers are separated
  5. extractionthe water layer is extracted with an additional 230 ml
  6. washwashed with 250 ml
  7. dry with materialof water, dried over sodium sulfate
  8. customthe solvent is removed by distillation through a short vigreau column at atmosphere pressure
  9. distillationdistilled at from 8.6 to 9.0 mm. of Hg
  10. customtaken at 112° to 128° C.

Sources & evidence

ORD record
ord-e2dc30b979fb4f3da187e0c38da092d5
Source dataset
uspto-grants-1977_12
Patent number
US04062952

Reaction notes

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