Hexylamine → N-Hexylperfluorobutanesulfonamide

HRID 2101253Notes

Reaction equation

HRID 2101253 reaction equation
[C:1]([S:14](F)(=[O:16])=[O:15])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[CH2:18]([NH2:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>O>[C:1]([S:14]([NH:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:16])=[O:15])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 8102HexylamineHCID 8471TriethylamineHCID 67814Perfluoro-1-butanesulfonyl fluoride

Product 1

HCID 85868528N-HexylperfluorobutanesulfonamideYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A 2-liter flask fitted with a thermocouple, overhead stirrer, dropping funnel and heating mantle was charged with C4F9SO2F (543 g, 1.80 mole). To this stirred material was slowly added a mixture of hexylamine (194.0 g, 1.90 mole) and triethylamine (194.0 g, 1.90 mole); the ensuing mixture was stirred and heated at 65° C. for 2 hours. Water (555.0 g) was then added, and stirred for an additional 30 minutes. The lower phase was separated, put into a flask and heated to 60° C. To this heated mixture was added sulfuric acid (50 g concentrated sulfuric and 500 g water). The lower phase of the resulting two-phase mixture was then separated, washed with water (500 g), and placed in a flask with a one-plate distillation head. The flask was heated to 80° C. at 20-25 mm Hg (2.7-3.3 kPa) and the distillate collected over a period of one hour. The material that remained in the flask was further distilled at 8 mm Hg (0.4 kPa) and a pot temperature of 138-143° C., yielding C4F9SO2NH(CH2)5CH3 (561.0 g). NMR and GC/MS analyses were consistent with the indicated material.

Workup

  1. customA 2-liter flask fitted with a thermocouple, overhead stirrer
  2. temperatureheating mantle
  3. additionTo this stirred material was slowly added
  4. stirringstirred for an additional 30 minutes
  5. customThe lower phase was separated
  6. customput into a flask
  7. temperatureheated to 60° C
  8. additionTo this heated mixture was added sulfuric acid (50 g concentrated sulfuric and 500 g water)
  9. customThe lower phase of the resulting two-phase mixture was then separated
  10. washwashed with water (500 g)
  11. distillationplaced in a flask with a one-plate distillation head
  12. temperatureThe flask was heated to 80° C. at 20-25 mm Hg (2.7-3.3 kPa)
  13. distillationthe distillate collected over a period of one hour
  14. distillationwas further distilled at 8 mm Hg (0.4 kPa)

Sources & evidence

ORD record
ord-3da92496786e4819bb0d603da93bbb90
Source dataset
uspto-grants-2009_08
Patent number
US07572848B2

Reaction notes

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