1,6-Dichlorohexane → 1,6-Bis-(N-acetyl-N-cyanoamino)-hexane

HRID 2290967Notes

Reaction equation

HRID 2290967 reaction equation
[C:1]([NH:4][C:5]#[N:6])(=[O:3])[CH3:2].[Na].Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Cl>CN(C)C=O>[C:1]([N:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:4]([C:5]#[N:6])[C:1](=[O:3])[CH3:2])[C:5]#[N:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 165511,6-DichlorohexaneHCID 57358861Sodium acetylcyanamide

Product 1

HCID 201539451,6-Bis-(N-acetyl-N-cyanoamino)-hexane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

106.1 g (1.0 mol) of sodium acetylcyanamide and 77.5 g (0.5 mol) of 1,6-dichlorohexane are reacted in 750 ml of dimethylformamide at 146°-147° C. for 8 hours, the mixture is then filtered with suction and the filtrate is concentrated on a rotary evaporator at 80° C. in vacuo. 125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5), are obtained. The yield of pure substance is 58.8 g (46.9% of theory) and the product has a melting point of 59°-61° C.

Workup

  1. filtrationthe mixture is then filtered with suction
  2. concentrationthe filtrate is concentrated on a rotary evaporator at 80° C. in vacuo
  3. custom125 g (99.9% of theory) of a crude product, which is recrystallised from a mixture of acetone/diisopropyl ether (3:5)
  4. customare obtained

Sources & evidence

ORD record
ord-152aa15cdf7b4845a46c1e212cf8a085
Source dataset
uspto-grants-1986_10
Patent number
US04618712

Reaction notes

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