Sulfuric Acid → HCID 41717, compound

HRID 2071809Notes

Reaction equation

HRID 2071809 reaction equation
S(=O)(=O)(O)O.[CH2:6]([C:8]([CH2:16][CH2:17][CH3:18])([CH2:12][CH2:13][CH2:14][CH3:15])C(O)=O)[CH3:7].[N-:19]=[N+]=[N-].[Na+].[OH-].[Na+]>CCOCC.C(Cl)(Cl)Cl>[CH2:6]([C:8]([NH2:19])([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13][CH2:14][CH3:15])[CH3:7]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 20341231HCID 20341231, compound

Product 1

HCID 41717HCID 41717, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

Into a three-necked flask equipped with a mechanical stirrer and a condenser, were introduced 70 ml of chloroform, 18 ml of concentrated sulphuric acid (d= 1.83) and 11 g (0.06 mol) of 2-ethyl-2-n-propylhexanoic acid prepared as described above. The mixture was heated to 50° C and while stirring 7.5 g of sodium azide in powder form were added. The operation of addition lasted 90 minutes after which the reaction mixture was heated to 50° C for 2 hours. The mixture was then neutralized with a 40% aqueous solution of sodium hydroxide previously cooled to 0° C. The amine was extracted with ether and the ethereal phase was washed with water and dried over magnesium sulphate. The ether was evaporated out under vacuum and the oil so obtained was taken up in dry ether, which provided 1-ethyl-1-n-propyl-n-pentylamine in free base form.

Workup

  1. customInto a three-necked flask equipped with a mechanical stirrer and a condenser
  2. customprepared
  3. additionwere added
  4. additionThe operation of addition
  5. temperatureafter which the reaction mixture was heated to 50° C for 2 hours
  6. temperaturepreviously cooled to 0° C
  7. extractionThe amine was extracted with ether
  8. washthe ethereal phase was washed with water
  9. dry with materialdried over magnesium sulphate
  10. customThe ether was evaporated out under vacuum
  11. customthe oil so obtained

Sources & evidence

ORD record
ord-69e9fbbbf8534b44a8ef5d3dedc34722
Source dataset
uspto-grants-1977_09
Patent number
US04048334

Reaction notes

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