Hydrochloric Acid → Methyl 2-(4-chlorophenylamino)-3-methylbutanimidate

HRID 1680139Notes

Reaction equation

HRID 1680139 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([CH:12]([CH3:14])[CH3:13])[C:10]#[N:11])=[CH:4][CH:3]=1.Cl.C[CH2:17][O:18]CC.C(=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]([CH:12]([CH3:14])[CH3:13])[C:10](=[NH:11])[O:18][CH3:17])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 127672192-(4-Chlorophenylamino)-3-methylbutyronitrile

Product 1

HCID 12767220Methyl 2-(4-chlorophenylamino)-3-methylbutanimidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.86 g (20 mmol) of 2-(4-chlorophenylamino)-3-methylbutyronitrile in 10 ml of methanol is saturated at reflux with hydrogen chloride gas. When all of the starting nitrile has been consumed, most of the methanol and excess hydrogen chloride is removed in vacuo. Ether is added to precipitate the hydrochloride of methyl 2-(4-chlorophenyl)-3-methylbutanimidate, which is isolated by filtration under nitrogen. The white solid is added with vigorous stirring to an ice-cold mixture of ether and aqueous sodium bicarbonate. The aqueous layer is discarded, and the ethereal layer is washed with cold water and dried over sodium sulfate. Filtration and concentration in vacuo gives methyl 2-(4-chlorophenylamino)-3-methylbutanimidate.

Workup

  1. customWhen all of the starting nitrile has been consumed, most of the methanol and excess hydrogen chloride
  2. customis removed in vacuo
  3. additionEther is added
  4. customto precipitate the hydrochloride of methyl 2-(4-chlorophenyl)-3-methylbutanimidate
  5. customwhich is isolated by filtration under nitrogen
  6. additionThe white solid is added
  7. washthe ethereal layer is washed with cold water
  8. dry with materialdried over sodium sulfate
  9. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-ed3b6ea43aaf4fa093c7d40e1deeb98a
Source dataset
uspto-grants-1981_06
Patent number
US04272449

Reaction notes

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