Diethanolamine → HCID 86607099, compound

HRID 900870Notes

Reaction equation

HRID 900870 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].[C:8]([NH:11][C:12]1[S:13][C:14]([S:18](Cl)(=[O:20])=[O:19])=[C:15]([CH3:17])[N:16]=1)(=[O:10])[CH3:9].C(N(CC)CC)C>O1CCOCC1>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[S:18]([C:14]1[S:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[N:16][C:15]=1[CH3:17])(=[O:19])=[O:20]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 8471TriethylamineHCID 969512-Acetamido-4-methylthiazole-5-sulfonyl chloride

Product 1

HCID 86607099HCID 86607099, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of diethanolamine (1.24 g, 11.8 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) commercially available 2-acetamido-4-methyl-thiazole-5-sulfonyl chloride (1.0 g, 3.93 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 bis-(2-hydroxy-ethyl)-amide (0.74 g, 58%) as a white solid. MS (ISP) 324.0 [(M+H)+]; mp 204° 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-5204fa72e49a41e4a5a05b0e6cd98bc2
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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