2-(Methylamino)ethanol → HCID 86607110, compound

HRID 900888Notes

Reaction equation

HRID 900888 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[C:6]([NH:9][C:10]1[S:11][C:12]([S:16](Cl)(=[O:18])=[O:17])=[C:13]([CH3:15])[N:14]=1)(=[O:8])[CH3:7].C(N(CC)CC)C>C1COCC1>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[S:16]([C:12]1[S:11][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[N:14][C:13]=1[CH3:15])(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 86607110HCID 86607110, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(methylamino)-ethanol (0.44 g, 5.86 mmol) in THF (12 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (1.0 g, 3.92 mmol) and triethylamine (0.6 ml, 4.32 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by flash chromatography on silica gel (dichloromethane/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-ethyl)-methyl-amide (0.93 g, 81%) as a white solid. MS (ISP) 294.0 [(M+H)+]; mp 189° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography on silica gel (dichloromethane/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-b7e58f02b7b44dbfbdf538db46dc1452
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

Loading…