2-Acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide → HCID 86607105, compound

HRID 900879Notes

Reaction equation

HRID 900879 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][CH:11]=1)(=[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][CH:11]=1)(=[O:9])=[O:8])([CH3:5])[CH3:4]

Participants

3

Reactant 1

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

Product 1

HCID 86607105HCID 86607105, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 2-acetamido-thiazole-5-sulfonic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide (0.68 g, 2.32 mmol) in 6N hydrochloric acid (20 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 (0.42 g, 72%) as a colorless oil. MS (ISP) 250.0 [(M−H)−].

Workup

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

Sources & evidence

ORD record
ord-af4fa95004fc41a0b2dbe25f2a7b1d7a
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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