Dimethylformamide → HCID 86735573, compound

HRID 1679692Notes

Reaction equation

HRID 1679692 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[N:15][OH:16])[CH2:10][CH2:11][CH2:12][C:13]#[N:14])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.Cl[CH2:19][CH2:20][NH2:21].[OH-].[K+].CN(C)C=O>Cl>[ClH:1].[NH2:21][CH2:20][CH2:19][O:16][N:15]=[C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:10][CH2:11][CH2:12][C:13]#[N:14]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14797Potassium HydroxideHCID 97937372-Chloroethylamine hydrochlorideHCID 86735581HCID 86735581, compound

Product 1

HCID 86735573HCID 86735573, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5.0 mmol (1.29 g) of 3', 4'-dichloro-4-cyanobutyrophenone oxime (melting point 122°-123° C), 5.2 mmol (0.60 g) of 2-chloroethylamine hydrochloride and 0.7 g of powdered potassium hydroxide were added, in this sequence and while stirring at 10° C, to 12 ml of dimethylformamide (D.M.F). After stirring for 2 days at room temperature the D.M.F. was evaporated invacuo, the residue was brought in water and 2N hydrochloric acid was then added while stirring until pH 3. The remaining oxime was removed by means of ether. The acid aqueous solution was then rendered alkaline with 15 ml of 2N sodium hydroxide solution and then extracted three times with ether. After washing with a 5% sodium bicarbonate solution, drying over sodium sulphate and evaporating the ether, the free base was obtained. This was dissolved in alcoholic hydrochloric acid. After evaporating the ethonal, the above entitled compound was crystallized from isopropanol/ether (1 : 1). Melting point 129°-130° C.

Workup

  1. customwas evaporated invacuo
  2. addition2N hydrochloric acid was then added
  3. customThe remaining oxime was removed by means of ether
  4. extractionextracted three times with ether
  5. washAfter washing with a 5% sodium bicarbonate solution
  6. dry with materialdrying over sodium sulphate
  7. customevaporating the ether
  8. customthe free base was obtained
  9. customAfter evaporating the ethonal, the
  10. customwas crystallized from isopropanol/ether (1 : 1)

Sources & evidence

ORD record
ord-feadc604f4ef42ddad2ebf52325797d2
Source dataset
uspto-grants-1978_03
Patent number
US04081552

Reaction notes

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