2-Acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide → 2-Amino-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide

HRID 900865Notes

Reaction equation

[OH:1][CH2:2][C:3]([NH:6][S:7]([C:10]1[S:14][C:13]([NH:15]C(=O)C)=[N:12][C:11]=1[CH3:19])(=[O:9])=[O:8])([CH3:5])[CH3:4]>Cl>[OH:1][CH2:2][C:3]([NH:6][S:7]([C:10]1[S:14][C:13]([NH2:15])=[N:12][C:11]=1[CH3:19])(=[O:9])=[O:8])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (1.15 g, 3.58 mmol) in 6N hydrochloric acid (14 ml) was heated for 2 h at 80° C., evaporated., and saturated NaHCO3 solution (30 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1) to yield the title compound (0.68 g, 71%) as a white solid. MS (ISP) 264.0 [(M−H)−]; mp 146° C.

Workup

customevaporated
addition, and saturated NaHCO3 solution (30 ml) was added
extractionThe mixture was extracted with ethyl acetate (3×50 ml)
washthe combined organic layers washed with brine (30 ml)
dry with materialdried (MgSO4)
customevaporated
customThe crude product was further purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 80:10:1)

Sources & evidence

ORD record: ord-cbd33b9c27fb42999e3de7e43e240069
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07361659B2

Reaction notes

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