Hydrochloric Acid → HCID 54286973, compound

HRID 1731242Notes

Reaction equation

HRID 1731242 reaction equation
[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[F:23][C:24]([F:31])([F:30])[C:25]([F:29])=[C:26](F)[F:27].Cl>CCOCC.CCCCCC.O>[C:1]([NH:5][S:6]([C:9]1[S:10][C:11]([Si:14]([CH3:17])([CH3:15])[CH3:16])=[CH:12][C:13]=1[C:26]([F:27])=[C:25]([F:29])[C:24]([F:31])([F:30])[F:23])(=[O:7])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8302HexafluoropropyleneHCID 13562682N-tert-Butyl-5-(trimethylsilyl)thiophene-2-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 54286973HCID 54286973, compoundYield 55.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

Two grams of the N-tert-butyl-5-trimethylsilyl-2-thiophenesulfonamide prepared in (1) above was dissolved in 100 ml of dry ether under nitrogen stream. To the solution, 15 ml of a 1.6M solution of n-butyllithium in n-hexane was added dropwise at 10° to 15° C., followed by stirring at room temperature for 4 hours. Subsequently, a dry ice condenser was attached to the reactor, and then 10 g of hexafluoropropene was charged at 0° to 10° C. under nitrogen stream. Reaction was performed under stirring for 3 hours. After completion of the reaction, the resulting product was poured into water, acidified with hydrochloric acid and extracted with ether. The ether layer was washed with water and dried. After distilling off ether under vacuum, the residue was purified by column chromatography on silica gel (eluent: methylene chloride) to provide 1.6 g of N-tert-butyl-3-(1,2,3,3,3-pentafluoropropen-1-yl)-5-trimethylsilyl-2-thiophenesulfonamide having a melting point of 92° to 94° C.

Workup

  1. customSubsequently, a dry ice condenser was attached to the reactor
  2. customReaction
  3. stirringunder stirring for 3 hours
  4. customAfter completion of the reaction
  5. extractionextracted with ether
  6. washThe ether layer was washed with water
  7. customdried
  8. distillationAfter distilling off ether under vacuum
  9. customthe residue was purified by column chromatography on silica gel (eluent: methylene chloride)

Sources & evidence

ORD record
ord-790238d25b9a484493042ed2aa560f76
Source dataset
uspto-grants-1986_11
Patent number
US04620868

Reaction notes

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