Ethanolamine → HCID 86607102, compound

HRID 900874Notes

Reaction equation

HRID 900874 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([NH:8][C:9]1[S:10][C:11]([S:15](Cl)(=[O:17])=[O:16])=[C:12]([CH3:14])[N:13]=1)(=[O:7])[CH3:6].C(N(CC)CC)C>O1CCOCC1>[OH:2][CH2:1][CH2:3][NH:4][S:15]([C:11]1[S:10][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[N:13][C:12]=1[CH3:14])(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 86607102HCID 86607102, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethanolamine (1.08 g, 17.7 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methylthiazole-5-sulfonyl chloride (1.5 g, 5.89 mmol) and triethylamine (0.9 ml, 6 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 (ethyl acetate/MeOH) and subsequent crystallization (dichloromethane/MeOH/hexane) to yield 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-ethyl)-amide (1.0 g, 61%) as a white solid. MS (ISP) 278.0 [(M−H)−]; mp 211° C.

Workup

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

Sources & evidence

ORD record
ord-5ddda90d796c49ccbedf8a7dbacb4df4
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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