Sodium Carbonate → HCID 20196917, compound

HRID 652797Notes

Reaction equation

HRID 652797 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:12]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=2)[OH:13])=[CH:4][CH:5]=1)#[N:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 869964-(Bromomethyl)benzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 20196917HCID 20196917, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 grams of alpha-bromo-p-cyanotoluene, 1.77 grams of hydroxylamine hydrochloride and 10.6 grams of anhydrous sodium carbonate in 50 ml of dry N,N-dimethylformamide (DMF) is allowed to stand overnight at room temperature. The DMF solvent is then removed under reduced pressure and the reidue is partitioned between methylene chloride and water. The organic layer is washed with water, dried over anhydrous sodium sulfate and then evaporated in vacuo to give a solid residue which upon trituration with ethanol yields the above-named compound as a white solid, melting at 172°-175° C.

Workup

  1. customThe DMF solvent is then removed under reduced pressure
  2. customthe reidue is partitioned between methylene chloride and water
  3. washThe organic layer is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customto give a solid residue which upon trituration with ethanol

Sources & evidence

ORD record
ord-2a5a4e5393644f268b8e45e0f7a71f1f
Source dataset
uspto-grants-1987_06
Patent number
US04673700

Reaction notes

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