Triethylamine → 1-(2-Acetylaminoethyl)-2,5-dimethyl-3-methylsulphinylpyrrole

HRID 1089436Notes

Reaction equation

HRID 1089436 reaction equation
[CH3:1][S:2](Cl)=[O:3].[C:5]([NH:8][CH2:9][CH2:10][N:11]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]1[CH3:17])(=[O:7])[CH3:6].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:5]([NH:8][CH2:9][CH2:10][N:11]1[C:12]([CH3:17])=[CH:13][C:14]([S:2]([CH3:1])=[O:3])=[C:15]1[CH3:16])(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 548463Methanesulfinyl chlorideHCID 13770049N-(2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl)acetamide

Product 1

HCID 145367551-(2-Acetylaminoethyl)-2,5-dimethyl-3-methylsulphinylpyrrole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

19.7 g (0.2 mol) of methylsulphinyl chloride are dissolved in 500 ml of methylene chloride. 36.0 g (0.2 mol) of 1-(2-acetylaminoethyl)-2,5-dimethylpyrrole and 27.6 ml (0.2 mol) of triethylamine in 500 ml of methylene chloride are added dropwise at 0° C. and the mixture is stirred at 0° C. for 45 minutes and poured onto aqueous sodium bicarbonate solution. The organic phase is separated off and discarded. The aqueous phase is concentrated and the residue is boiled up with isopropanol and, after the mixture has been concentrated, the product is chromatographed.

Workup

  1. customThe organic phase is separated off
  2. concentrationThe aqueous phase is concentrated
  3. concentrationafter the mixture has been concentrated
  4. customthe product is chromatographed

Sources & evidence

ORD record
ord-4f539bc04d6443cdaa8a93904c4f8384
Source dataset
uspto-grants-1990_10
Patent number
US04966901

Reaction notes

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