Hypofluorous acid, trifluoromethyl ester → HCID 21427924, compound

HRID 437319Notes

Reaction equation

HRID 437319 reaction equation
[NH2:1][CH:2]1[NH:9][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.[F:10]OC(F)(F)F.FC1(F)CCCCNC1=O.FC1CCCNC(=O)C1(F)F>>[F:10][CH:6]1[CH2:5][CH2:4][CH2:3][CH:2]([NH2:1])[NH:9][C:7]1=[O:8]

Participants

5

Reactant 4

HCID 78989Hypofluorous acid, trifluoromethyl esterHCID 18706036HCID 18706036, compoundHCID 21427941HCID 21427941, compoundHCID 21427944HCID 21427944, compound

Product 1

HCID 21427924HCID 21427924, compound

Procedure

ε-Aminocaprolactam (2.26 g., 0.02 mole) is dissolved in 60 ml. of liquid HF. Fluoroxytrifluoromethane (10.4 g., 0.1 mole) is passed into the solution under ultraviolet irradiation over 51/2 hours, while kept under vigorous stirring in a dry-ice-acetone cooling bath. After 11/2 hours more ultraviolet irradiation under similar conditions, the solvent is removed by distillation. The residue is quenched with ice and water and extracted 3 times with ethyl acetate. The combined extracts are washed with aqueous sodium bicarbonate solution, dried over magnesium sulfate and evaporated to dryness, to give a mixture of C-fluorinated caprolactams, with the main components being difluorocaprolactam and trifluoro-caprolactam.

Workup

  1. customAfter 11/2 hours more ultraviolet irradiation under similar conditions
  2. customthe solvent is removed by distillation
  3. customThe residue is quenched with ice and water
  4. extractionextracted 3 times with ethyl acetate
  5. washThe combined extracts are washed with aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness
  8. customto give

Sources & evidence

ORD record
ord-7d1fae59bebd4d318f3b3b0ecb3ba3ec
Source dataset
uspto-grants-1977_06
Patent number
US04030994

Reaction notes

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