4-Toluenesulfonyl chloride → HCID 20523222, compound

HRID 127922Notes

Reaction equation

HRID 127922 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH:6]([NH:8][CH2:9][CH:10]([O:13][CH3:14])[O:11][CH3:12])[CH3:7].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH:6]([N:8]([CH2:9][CH:10]([O:11][CH3:12])[O:13][CH3:14])[S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:7]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 20523216HCID 20523216, compound

Product 1

HCID 20523222HCID 20523222, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
25 °C

Procedure

A mixture of 23.9 g. (0.1 mole) of 3-methoxy-α-methyl-N-(2,2-dimethoxyethyl)benzylamine in 100 ml. of dry pyridine is stirred, cooled and treated with a solution of 20.2 g. (0.107 mole) of tosyl chloride in 100 ml. of dry pyridine. The mixture is stirred at 25° C. for three days, poured into 800 ml. of water and extracted with ether. The combined ether extracts are washed with dilute hydrochloric acid and then with water, dried, filtered and evaporated to yield 3-methoxy-α-methyl-N-(2,2-dimethoxyethyl)-N-tosyl-benzylamine.

Workup

  1. additionA mixture of 23.9 g
  2. temperaturecooled
  3. additiontreated with a solution of 20.2 g
  4. additionpoured into 800 ml
  5. extractionof water and extracted with ether
  6. washThe combined ether extracts are washed with dilute hydrochloric acid
  7. dry with materialwith water, dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-30188f972d4547309a1758fa2af52d56
Source dataset
uspto-grants-1981_03
Patent number
US04258049

Reaction notes

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