Trimethylamine → Methyl 3-[2-[2-(5-methyl-2-thienyl)ethoxy]ethylaminosulphonyl]propanoate

HRID 613747Notes

Reaction equation

HRID 613747 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.CN(C)C.Cl[S:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])(=[O:20])=[O:19]>ClCCl>[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][NH:12][S:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])(=[O:20])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 4962888Methyl 3-(chlorosulfonyl)propanoateHCID 195934942-[2-(5-Methyl-2-thienyl)ethoxy]ethanamine

Product 1

HCID 18779053Methyl 3-[2-[2-(5-methyl-2-thienyl)ethoxy]ethylaminosulphonyl]propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of step c) as the hydrochloride salt (1.50 g) was stirred under nitrogen in dichloromethane (25 ml). Trimethylamine (2.21 ml) was added followed by methyl 3-(chlorosulphonyl)propanoate (1.18 g). The mixture was stirred at room temperature overnight. The solution was diluted with a further amount of dichloromethane and the organics washed with dilute hydrochloric acid then water, then dried (MgSO4). The mixture was filtered and the volatiles removed in vacuo to give the subtitle compound as an oil (1.4 g).

Workup

  1. washthe organics washed with dilute hydrochloric acid
  2. dry with materialwater, then dried (MgSO4)
  3. filtrationThe mixture was filtered
  4. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-1dbb62a917d041cc8842c69e3cb41c8b
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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