4-Nitrobenzoyl chloride → HCID 12115458, compound

HRID 2086324Notes

Reaction equation

HRID 2086324 reaction equation
[NH:1]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].I[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O>C(OC)(C)(C)C.O.O1CCCC1>[CH2:17]([N:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 11430Potassium Carbonate2×HCID 336431-IodopropaneHCID 14669946HCID 14669946, compound

Product 1

HCID 12115458HCID 12115458, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6,6′-imino-bis-capronitrile (20.7 g, 100 mmol), 1-iodopropane (18.7 g 110 mmol), potassium carbonate (16.6 g, 120 mmol), and 100 mL of tetrahydrofuran was stirred and heated at 60° C. under nitrogen for three days. The product mixture was cooled to room temperature, and 25 mL of water was added to dissolve most of the solids. The aqueous layer was drawn off in a separatory funnel, a 125-mL portion of methyl t-butyl ether was added, and another small aqueous layer thus formed was drawn off. Gas chromatographic analysis of the product solution showed it to contain a small amount of unreacted secondary amine. Therefore, 10 g of anhydrous potassium carbonate and 2.5 g of 4-nitrobenzoyl chloride were added, and the mixture was stirred at room temperature for 30 minutes. Subsequent analysis by gas chromatography showed this treatment to have completely eliminated the unreacted starting material. The mixture was filtered, and solvent was removed by rotary evaporation at reduced pressure. Molecular distillation of the residue under high vacuum afforded 20.2 g (81 mmol, 81% of theory) of 6,6′-propylimino-bis-capronitrile.

Workup

  1. temperatureThe product mixture was cooled to room temperature
  2. dissolutionto dissolve most of the solids
  3. customThe aqueous layer was drawn off in a separatory funnel
  4. customanother small aqueous layer thus formed
  5. stirringthe mixture was stirred at room temperature for 30 minutes
  6. filtrationThe mixture was filtered
  7. customsolvent was removed by rotary evaporation at reduced pressure
  8. distillationMolecular distillation of the residue under high vacuum

Sources & evidence

ORD record
ord-1dcc5eed42094d3986489947dceba4a9
Source dataset
uspto-grants-2004_04
Patent number
US06723799B2

Reaction notes

Loading…