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

HRID 1457041Notes

Reaction equation

HRID 1457041 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.C(N(CC)CC)C.Cl[S:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])(=[O:23])=[O:22]>ClCCl>[CH3:1][C:2]1[S:6][C:5]([CH2:7][CH2:8][O:9][CH2:10][CH2:11][NH:12][S:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])(=[O:23])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 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). Triethylamine (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-54990df4efd2419d80cc7ca14802fba0
Source dataset
uspto-grants-1998_12
Patent number
US05846989

Reaction notes

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