4-Toluenesulfonyl chloride → HCID 595083, compound

HRID 1971460Notes

Reaction equation

HRID 1971460 reaction equation
[Cl-].[Cl:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[NH2+:5].C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(#N)C.ClCCl>[Cl:2][CH2:3][C:4](=[N:5][S:25]([C:22]1[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=1)(=[O:27])=[O:26])[N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178479569HCID 178479569, compound

Product 1

HCID 595083HCID 595083, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
7.5 °C

Procedure

To 1 g (5.02 mmol) 2-chloro-1-morpholine-4-ylethaniminium chloride and 0.7 ml triethylamine in 25 ml acetonitrile were added 0.96 g p-toluene sulfonic acid chloride at 10° C. and the mixture was stirred for 2 hours at 5-10° C. For workup, the mixture was diluted with dichlormethane, was washed with water and saturated NaCl-solution, was dried with MgSO4, was filtered and was evaporation-concentrated. Chromatography on silica gel (dichlormethane/methanol 0-3%) yielded 400 mg of the target products; ESI-MS [M+H+]=317.05.

Workup

  1. washwas washed with water and saturated NaCl-solution
  2. dry with materialwas dried with MgSO4
  3. filtrationwas filtered
  4. concentrationwas evaporation-concentrated

Sources & evidence

ORD record
ord-263878443f0e4be9b176b6040b83f8f2
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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