Water → HCID 18796452, compound

HRID 582870

Reaction equation

HRID 582870 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([N+]([O-])=O)[CH:14]=1.O>CN(C)C=O>[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67180Acetone, oximeHCID 969244-Chloro-2-nitrobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 18796452HCID 18796452, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 75 ml of dry N,N-dimethylformamide was dissolved acetone oxime (1.21 g), followed by potassium tertiary butoxide (1.85 g) and stirred under nitrogen. After 30 minutes, 4-chloro-2-nitro-benzonitrile (2.00 g) was added. After an additional 30 minutes the reaction was poured into water (500 ml) and filtered. The solid was collected and dissolved in DCM (250 ml), dried (MgSO4), and concentrated in vacuo. The resulting solid was recrystallized from ethanol to yield 1.5 g of the product, m.p. 83-84° C.

Workup

  1. filtrationfiltered
  2. customThe solid was collected
  3. dissolutiondissolved in DCM (250 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-b0496799b6cd46ba84d9201c0b9b6e22
Source dataset
uspto-grants-1999_07
Patent number
US05925766

Linked notes

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