Water → HCID 19785216, compound

HRID 256529Notes

Reaction equation

HRID 256529 reaction equation
[H-].[Na+].[F:3][C:4]([F:25])([F:24])[C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:14]=[CH:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:11]=1)=[O:6].[CH3:26]I.O>CN(C)C=O>[CH3:26][N:7]([CH2:8][CH2:9][C:10]1[CH:14]=[CH:13][N:12]([S:15]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH:11]=1)[C:5](=[O:6])[C:4]([F:24])([F:3])[F:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19785215HCID 19785215, compound

Product 1

HCID 19785216HCID 19785216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

50% Sodium hydride oil dispersion (0.62 g) was added to an ice-cooled solution of N-trifluoroacetyl-2-(1-phenylsulphonyl-3-pyrrolyl)ethylamine (3.59 g) in dimethylformamide (20 ml) after 20 minutes, methyl iodide (1.76 g) was added and the mixture was heated at 70° C. overnight. After cooling, water was added and the mixture was extracted with ether 3 times. The ether was washed with water, dried and evaporated to give N-methyl-N-trifluoroacetyl-2-(1-phenylsulphonyl-3-pyrrolyl)ethylamine as an oil. The oil was dissolved in methanol (40 ml), 0.880 ammonia added and the solution was stirred for 6 hours. After evaporation, the residue was dissolved in 5M hydrochloric acid and extracted with ether. The aqueous part was basified with 0.880 ammonia and the product was extracted into dichloromethane. The extracts were washed with water, dried and evaporated to give the title product as a pure oil.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ether 3 times
  3. washThe ether was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-157f74a4f61248e2aea721ae11f292a8
Source dataset
uspto-grants-1993_11
Patent number
US05258378

Reaction notes

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