1,4-Dichloro-cis-2-butene → cis-1,4-Bis-(N-acetyl-N-cyanoamino)-but-2-ene

HRID 2290968Notes

Reaction equation

HRID 2290968 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]\[CH2:5]Cl.[C:7]([NH:10][C:11]#[N:12])(=[O:9])[CH3:8].[Na]>CC(N(C)C)=O>[C:7]([N:10]([CH2:2]/[CH:3]=[CH:4]\[CH2:5][N:10]([C:11]#[N:12])[C:7](=[O:9])[CH3:8])[C:11]#[N:12])(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 64321151,4-Dichloro-cis-2-buteneHCID 57358861Sodium acetylcyanamide

Product 1

HCID 86741084cis-1,4-Bis-(N-acetyl-N-cyanoamino)-but-2-ene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

25.0 g (0.2 mol) of cis-1,4-dichlorobut-2-ene and 46.7 g (0.4 mol+10% excess) of sodium acetylcyanamide are reacted in 80 ml of dimethylacetamide at 70°-88° C. for 4 hours. The reaction mixture is then filtered with suction, the filtrate is introduced into 400 g of ice and the resulting suspension is filtered. The residue is dried over phosphorus pentoxide at room temperature under 0.13 mbar to give 29.4 g (66.7% of theory) of the desired compound, which has a melting point of 73.8°-75.2° C.

Workup

  1. filtrationThe reaction mixture is then filtered with suction
  2. additionthe filtrate is introduced into 400 g of ice
  3. filtrationthe resulting suspension is filtered
  4. dry with materialThe residue is dried over phosphorus pentoxide at room temperature under 0.13 mbar

Sources & evidence

ORD record
ord-f623e35f1c59459d8fcc4f6b8b443731
Source dataset
uspto-grants-1986_10
Patent number
US04618712

Reaction notes

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