Crotononitrile → 3-Methyl-2-morpholino-2-(alpha,alpha,alpha-trifluoro-m-tolyl)glutaronitrile

HRID 1763610

Reaction equation

HRID 1763610 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]#[N:11])[CH:4]=1.[OH-].[K+].C(O)C.[C:25](#[N:29])/[CH:26]=[CH:27]/[CH3:28]>O1CCCC1>[CH3:28][CH:27]([CH2:26][C:25]#[N:29])[C:9]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)([C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:18])[F:19])[CH:8]=[CH:7][CH:6]=1)[C:10]#[N:11]

Participants

5

Reactant 3

HCID 637921CrotononitrileHCID 36941922-Morpholino-2-[3-(trifluoromethyl)phenyl]acetonitrileHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 124495173-Methyl-2-morpholino-2-(alpha,alpha,alpha-trifluoro-m-tolyl)glutaronitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of α-(α,α,α-trifluoro-m-tolyl)-4-morpholineacetonitrile in 100 ml. of tetrahydrofuran is added 1.0 ml. of 30% KOH-ethanol solution. To the mixture is added 2.56 g. of crotononitrile and the mixture is stirred at room temperature for 18 hrs. The mixture is concentrated to dryness under vacuum and the residue is dissolved in chloroform. The solution is passed through a column of hydrous magnesium silicate. The eluent is concentrated to an oil (17.3 g) which is crystallized from hexane and recrystallized from CHCL3 -hexane to give 3-methyl-2-morpholino-2-(α,α,α-trifluoro-m-tolyl)glutaronitrile as crystals, m.p. 115°-118° C.

Workup

  1. additionTo the mixture is added 2.56 g
  2. concentrationThe mixture is concentrated to dryness under vacuum
  3. dissolutionthe residue is dissolved in chloroform
  4. concentrationThe eluent is concentrated to an oil (17.3 g) which
  5. customis crystallized from hexane
  6. customrecrystallized from CHCL3 -hexane

Sources & evidence

ORD record
ord-6baa0556377e44a7821e68c108ea8bbc
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Linked notes

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