Water → HCID 57871042, compound

HRID 2191160Notes

Reaction equation

HRID 2191160 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-d037f3de08864779bcd5f20e2b59349b
Source dataset
uspto-grants-2012_12
Patent number
USRE043858E1

Reaction notes

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