4-Chlorobenzenesulfonyl chloride → HCID 14152352, compound

HRID 1085209Notes

Reaction equation

HRID 1085209 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][CH2:9][C:10]1[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>O1CCOCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([NH:7][CH2:8][CH2:9][C:10]2[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 5650581-methyl-1H-pyrrole-2-ethylamine

Product 1

HCID 14152352HCID 14152352, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

10 ml of a saturated potassium carbonate solution are added to a solution of 4.96 g of 2-(2-aminoethyl)-1-methylpyrrole in 20 ml of dioxane, with stirring. Then at 0° C. a solution of 10.1 g of p-chlorobenzene sulphonylchloride in 30 ml of dioxane is added dropwise. The mixture is then stirred for 3 hours at ambient temperature, the precipitate is removed by suction filtering, washed with ether and the organic phase is separated off. After drying over sodium sulphate 10 g of crude product are obtained which is chromatographed over a silica gel column with methylene chloride/cyclohexane (9:1).

Workup

  1. stirringThe mixture is then stirred for 3 hours at ambient temperature
  2. customthe precipitate is removed by suction
  3. filtrationfiltering
  4. washwashed with ether
  5. customthe organic phase is separated off
  6. dry with materialAfter drying over sodium sulphate 10 g of crude product
  7. customare obtained which
  8. customis chromatographed over a silica gel column with methylene chloride/cyclohexane (9:1)

Sources & evidence

ORD record
ord-d21d6bc4e77d4e2da1694658afece00f
Source dataset
uspto-grants-1991_04
Patent number
US05008290

Reaction notes

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