4-Toluenesulfonyl chloride → HCID 10364722, compound

HRID 327533Notes

Reaction equation

HRID 327533 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][NH2:16])[CH2:7][O:8]2.C(N(CC)CC)C.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28]>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][NH:16][S:27]([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28])[CH2:7][O:8]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10333044HCID 10333044, compound

Product 1

HCID 10364722HCID 10364722, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4 mmol of the compound prepared in Example 14 are dissolved in 30 ml of dichloromethane cooled in ice. 11.4 mmol of triethylamine are added dropwise, followed by 4 mmol of tosyl chloride dissolved in dichloromethane. The mixture is left stirring for 30 minutes at room temperature. The solvent is then evaporated off and the expected product is obtained after purification by chromatography on a silica column (elution solvent: dichloromethane).

Workup

  1. temperaturecooled in ice
  2. waitThe mixture is left
  3. customThe solvent is then evaporated off

Sources & evidence

ORD record
ord-773035888a474290b0b93176ba49fee7
Source dataset
uspto-grants-1993_12
Patent number
US05273994

Reaction notes

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