Water → HCID 57871042, compound

HRID 546348Notes

Reaction equation

HRID 546348 reaction equation
[N:1]1([NH2:6])[CH:5]=[CH:4][CH:3]=[CH:2]1.C(N(CC)CC)C.Cl[S:15]([C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:17])=[O:16].O>C(OCC)(=O)C>[N:1]1([NH:6][S:15]([CH:18]2[C:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH2:21][CH2:22][CH2:23]2)(=[O:17])=[O:16])[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1365891-AminopyrroleHCID 11747135HCID 11747135, compound

Product 1

HCID 57871042HCID 57871042, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1.0 g (12.18 mmol) of 1H-pyrrol-1-ylamine and 1.8 ml (13.40 mmol) of triethylamine in 60 ml of ethyl acetate was added dropwise a solution of 3.6 g (12.18 mmol) of ethyl 2-chlorosulfonyl-1-cyclohexene-1-carboxylate (compound disclosed in the specification of Japanese Patent Application (Kokai) No. 2000-178246) in 12 ml of ethyl acetate with stirring under ice-cooling, followed by stirring overnight at room temperature. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane:ethyl acetate=3:1) and the resulting solid was further washed with isopropyl ether to give 1.9 g of the title compound as a white powder (yield: 52%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. washthe resulting solid was further washed with isopropyl ether

Sources & evidence

ORD record
ord-806f303a2d0246989f7d0bf0cc239cd4
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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