4-Toluenesulfonyl chloride → HCID 15218866, compound

HRID 2226637Notes

Reaction equation

HRID 2226637 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:12]([N:14]([CH3:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13].C1(NC2CCCCC2)CCCCC1.[CH3:35][O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]O)=[CH:39][CH:38]=1>ClCCl>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O-:36])(=[O:3])=[O:2].[CH3:35][O:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][N+:14]([CH2:12][CH3:13])([CH3:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 7582DicyclohexylamineHCID 77384-Methoxybenzyl alcoholHCID 11956Benzenamine, N-ethyl-N-methyl-

Product 1

HCID 15218866HCID 15218866, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

19.07 g (0.1 mol) of tosyl chloride, 13.5 g (0.1 mol) of N-ethyl-N-methylaniline and 27.20 g (0.15 mol) of dicyclohexylamine were dissolved in 60 g of dichloromethane, and, after cooling to 5° C., there was added 13.81 g (0.1 mol) of 4-methoxybenzylalcohol. While suppressing excessive elevation of the temperature, the reaction was allowed for 6 hours. After the completion of the reaction, the mixture was concentrated, and the precipitated white solid was washed with ether and dried to give N-(4-methoxybenzyl)-N-ethyl-N-methyl-anilinium tosylate. Yield: 50%.

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe mixture was concentrated
  3. washthe precipitated white solid was washed with ether
  4. customdried

Sources & evidence

ORD record
ord-9f9365111fb946fc9f86c79e2a54176b
Source dataset
uspto-grants-1994_09
Patent number
US05349067

Reaction notes

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