2-(Dimethylamino)ethanol → HCID 70360573, compound

HRID 330408Notes

Reaction equation

HRID 330408 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][OH:8])[CH3:5].Cl.Cl[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21][NH:22][CH:23]([CH3:25])[CH3:24])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30]>CCCCCC.CS(C)=O>[C:26]([OH:33])(=[O:32])/[CH:27]=[CH:28]\[C:29]([OH:31])=[O:30].[CH3:3][N:4]([CH3:5])[CH2:6][CH2:7][O:8][C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH2:21][NH:22][CH:23]([CH3:25])[CH3:24])(=[O:18])=[O:19])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 444266Maleic AcidHCID 13655033N-[2-(4-chlorophenylsulfonyl)ethyl]-2-propanamine hydrochloride

Product 1

HCID 70360573HCID 70360573, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

A mixture of 0.124 mole of sodium hydride (4.96 g of a 60% dispersion in oil; washed with hexane) and 13 g (0.146 mole) of 2-(N,N-dimethylamino)ethanol in 400 ml of dimethyl sulfoxide was stirred at room temperature and under an atmosophere of nitrogen for approximately 0.5 hr. To this solution was added 15.4 g (0.0519 mole) of N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-1-methylethanamine hydrochloride [1:1] (from Preparation 23), and the mixture was stirred at 80°-100° C. for approximately 2 hr. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give a liquid. This was treated with approximately 0.1 mole of maleic acid, and the resulting salt was recrystallized from methanol-diethyl ether to give 22.83 g (80.6%) of the product as a white crystalline solid, mp 177.5°-178.5° C.

Workup

  1. stirringthe mixture was stirred at 80°-100° C. for approximately 2 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give a liquid
  7. customthe resulting salt was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-c29cf8642ff9497dab4cfcf668c7c19c
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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