4-Toluenesulfonyl chloride → HCID 73505384, compound

HRID 250168Notes

Reaction equation

HRID 250168 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16](O)[CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)=[N:14][CH:15]=1)[CH3:9].[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29]>ClCCl.O>[CH2:8]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]([S:28]([C:31]2[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)=[N:14][CH:15]=1)[CH3:9]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 115507874-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde

Product 1

HCID 73505384HCID 73505384, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

0.44 g (0.0044 mol) triethyl amine was added to a solution of 1 g (0.0036 mol) 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde and 0.7 g (0.0036 mol) tosyl chloride dissolved in 25 mL dichloromethane at 0-5° C. Reaction mixture was stirred at 0-5° C. for 4 hr. Progress of the reaction was monitored by TLC and after completion of reaction, substantial work-up in excess water yielded the desired product. Yield of the product was 1 g (70%).

Workup

  1. customReaction mixture

Sources & evidence

ORD record
ord-be2dce30b75c4bd2a80125001f757cae
Source dataset
uspto-grants-2011_01
Patent number
US07863300B2

Reaction notes

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