Pyridine → HCID 21996214, compound

HRID 1978067Notes

Reaction equation

HRID 1978067 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6](Cl)(=[O:8])=[O:7].[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[NH:11][NH2:12].N1C=CC=CC=1>C(OCC)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][S:6]([N:11]([NH2:12])[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 70091tert-Butyl carbazateHCID 742124-Chlorobutane-1-sulphonyl chloride

Product 1

HCID 21996214HCID 21996214, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 40 g of 4-chloro-1-butanesulphonyl chloride in 400 ml of diethyl ether was added dropwise to a solution of 30.4 g of tert-butyl carbazate and 17 ml of pyridine in 400 ml of diethyl ether at room temperature. The mixture was stirred at room temperature for 72 hours and then washed with water. The separated organic phase was dried over anhydrous magnesium sulphate. The oily residue obtained after evaporation of the solvent was purified by flash column chromatography on silica gel using hexane/ethyl acetate (8:2, increasing to 6:4) for the elution. 10.25 g of tert-butyl 2-[(4-chlorobutyl)sulphonyl]carbazate were obtained in the form of a white solid.

Workup

  1. washwashed with water
  2. dry with materialThe separated organic phase was dried over anhydrous magnesium sulphate
  3. customThe oily residue obtained
  4. customafter evaporation of the solvent
  5. customwas purified by flash column chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-f6bc80cc7d0e4dfc8957281a05004256
Source dataset
uspto-grants-2001_05
Patent number
US06235787B1

Reaction notes

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