Sulfuric Acid → HCID 58136859, compound

HRID 532368Notes

Reaction equation

HRID 532368 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:16]([CH3:23])[C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].[Br-:24].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.S(=O)(=O)(O)O>CO.C1COCC1.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>[Br:24][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([N:16]([CH3:23])[C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[CH:7]=[C:8]([S:10]([F:14])([F:15])([F:13])([F:12])[F:11])[CH:9]=1)=[O:3]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58136869N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide

Product 1

HCID 58136859HCID 58136859, compoundYield 164.6%

Reagents, catalysts & solvents 3

HCID 17977687Phenyltrimethylammonium bromide dibromideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide (O2.075; 1.03 g) was dissolved in a mixture of methanol (20 ml) and THF (20 ml). Phenyltrimethylammonium tribromide (1.05 g) was added while stirring. After stirring at RT for 5 h, the mixture was left to stand overnight, then further phenyltrimethylammonium tribromide (100 mg) was added and the mixture was heated to 60° C. for 2 h. After cooling, the reaction mixture was added to 2 N sulfuric acid and stirred for 10 min. Then the aqueous phase was extracted three times with EA. The combined organic phases were dried over magnesium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 1.2 g of the title compound were obtained, which had sufficient purity for the next reactions.

Workup

  1. stirringAfter stirring at RT for 5 h
  2. waitthe mixture was left
  3. temperatureAfter cooling
  4. stirringstirred for 10 min
  5. extractionThen the aqueous phase was extracted three times with EA
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. filtrationafter the desiccant had been filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-975a171d29054848bd474ab235e3c3a4
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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