Dimethylformamide → HCID 53960770, compound

HRID 1448718Notes

Reaction equation

HRID 1448718 reaction equation
[C:1]([CH:4]1[CH2:9][CH:8]2[CH2:10][CH:5]1[CH:6]=[CH:7]2)(=O)[CH3:2].[C:11](CC(O)=O)#[N:12].[OH-].[NH4+].[CH3:19]N(C)C=O>C1C=CC=CC=1>[C:11]([CH2:2][C:1](=[C:4]1[CH2:9][CH:8]2[CH2:10][CH:5]1[CH:6]=[CH:7]2)[CH3:19])#[N:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9740Cyanoacetic acidHCID 14923Ammonium HydroxideHCID 1073661-(Bicyclo[2.2.1]hept-5-en-2-yl)ethanone

Product 1

HCID 53960770HCID 53960770, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A stirred solution of 100 g (0.72 mol) of 2-acetyl-5-norbornene (Aldrich Chemical Co.), 65 g (0.76 mol) of cyanoacetic acid, 2 ml of ammonium hydroxide (58%), 132 ml of dimethylformamide; and 170 ml of benzene was heated to reflux and the water removed with a Dean-Stark trap. The reaction was allowed to continue until the evolution of carbon dioxide ceased (approx. 24 hr.). Upon completion the reaction was cooled and the solvent removed under reduced pressure. The residue oil was distilled under vacuum to give 36 g (31% yield) of 2-(2-cyano-1-methylethylidene)-bicyclo[2.2.1]hept-5-ene: b.p. 73°-84° C./1 mm; ir 3060, 2255, 2225, 1450, 1420, 1330, 905, 730, 715: nmr 1.2-2.2 (m), 2.7-3.4 (m), 5.0-6.1 (m, vinylic H); ms 159.

Workup

  1. temperatureto reflux
  2. customthe water removed with a Dean-Stark trap
  3. custom(approx. 24 hr.)
  4. temperatureUpon completion the reaction was cooled
  5. customthe solvent removed under reduced pressure
  6. distillationThe residue oil was distilled under vacuum

Sources & evidence

ORD record
ord-c130ee1c7fa54431ae63a5ccf383ae6b
Source dataset
uspto-grants-1980_02
Patent number
US04187243

Reaction notes

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