Triethylamine → 2-Acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 900878Notes

Reaction equation

HRID 900878 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[C:7]([NH:10][C:11]1[S:12][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:14][N:15]=1)(=[O:9])[CH3:8].C(N(CC)CC)C>O1CCOCC1>[OH:4][CH2:3][C:2]([NH:1][S:16]([C:13]1[S:12][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[N:15][CH:14]=1)(=[O:17])=[O:18])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 3502612-Acetamido-1,3-thiazole-5-sulfonyl chloride

Product 1

HCID 866071042-Acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amideYield 59%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2-amino-2-methyl-1-propanol (1.11 g, 12.5 mmol) in dioxane (20 ml) was added at 0° C. (ice water bath) 2-acetamido-thiazole-5-sulfonyl chloride [CAS No. 69812-30-2; commercially available] (1.0 g, 4.15 mmol) and triethylamine (0.64 ml, 4.57 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acetate) to yield 2-acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.72 g, 59%) as a white solid. MS (ISP) 292.1 [(M−H)−]; mp 206° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-53f020358d444c26824190e9707b4452
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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