Methanol → HCID 18671285, compound

HRID 1057274Notes

Reaction equation

HRID 1057274 reaction equation
[Na].CO.[CH2:4]([NH:6][S:7]([C:10]([F:34])([F:33])[C:11]([F:32])([F:31])[C:12]([F:30])([F:29])[C:13]([F:28])([F:27])[C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])(=[O:9])=[O:8])[CH3:5].[N:35]1[C:42](Cl)=[N:41][C:39](Cl)=[N:38][C:36]=1[Cl:37]>CC(C)=O>[Cl:37][C:36]1[N:35]=[C:42]([N:6]([CH2:4][CH3:5])[S:7]([C:10]([F:34])([F:33])[C:11]([F:31])([F:32])[C:12]([F:29])([F:30])[C:13]([F:27])([F:28])[C:14]([F:25])([F:26])[C:15]([F:23])([F:24])[C:16]([F:21])([F:22])[C:17]([F:20])([F:19])[F:18])(=[O:9])=[O:8])[N:41]=[C:39]([N:6]([CH2:4][CH3:5])[S:7]([C:10]([F:33])([F:34])[C:11]([F:31])([F:32])[C:12]([F:29])([F:30])[C:13]([F:27])([F:28])[C:14]([F:25])([F:26])[C:15]([F:23])([F:24])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])(=[O:9])=[O:8])[N:38]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7954Cyanuric chlorideHCID 77797N-Ethylperfluorooctane sulfonamideHCID 5360545Sodium

Product 1

HCID 18671285HCID 18671285, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-65 °C

Procedure

Metallic sodium (4.08 g, 177 mmols) was reacted with methanol (150 mls). N-Ethyl perfluorooctyl sulphonamide (93.28 g, 177 mmols) was added, and the resulting solution was stirred for 30 minutes. The methanol was removed at the pump (a vacuum pump was required to remove the final traces of solvent). The resulting sticky solid was dissolved in acetone (300 mls) and cooled to −65° C. under argon. Recrystalised cyanuric chloride (16.33 g, 88.5 mmols) dissolved in acetone (100 mls) was added to the reaction mixture dropwise such that the temperature did not rise above −50° C. (˜1 hour). After the addition, the reaction mixture was allowed to slowly warm to room temperature (1 hour) and then stirred for a further 3 hours. The precipated solid was removed by filtration and dried under vacuum. Purification by soxhlet extraction with acetone afforded 61 g (56.9%) of a fine white powder.

Workup

  1. customThe methanol was removed at the pump (a vacuum pump
  2. customto remove the final traces of solvent)
  3. dissolutionThe resulting sticky solid was dissolved in acetone (300 mls)
  4. additionwas added to the reaction mixture dropwise such that the temperature
  5. customdid not rise above −50° C.
  6. custom(˜1 hour)
  7. additionAfter the addition
  8. temperatureto slowly warm to room temperature (1 hour)
  9. stirringstirred for a further 3 hours
  10. customThe precipated solid was removed by filtration
  11. customdried under vacuum
  12. customPurification
  13. extractionby soxhlet extraction with acetone

Sources & evidence

ORD record
ord-a37bdfafb0604d8493ec84823f2c5e30
Source dataset
uspto-grants-2003_02
Patent number
US06514887B1

Reaction notes

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