HCID 86607102, compound → HCID 86607103, compound

HRID 900875Notes

Reaction equation

HRID 900875 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[S:12][C:11]([NH:13]C(=O)C)=[N:10][C:9]=1[CH3:17])(=[O:7])=[O:6]>Cl>[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[S:12][C:11]([NH2:13])=[N:10][C:9]=1[CH3:17])(=[O:6])=[O:7]

Participants

3

Reactant 1

HCID 86607102HCID 86607102, compound

Product 1

HCID 86607103HCID 86607103, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A stirred suspension of 2-acetamido-4-methyl-thiazole-5-sulfonic acid (2-hydroxy-ethyl)-amide (0.95 g, 3.4 mmol) in 6N hydrochloric acid (13 ml) was heated for 2 h at 80° C., evaporated, and saturated NaHCO3 solution (20 ml) was added. The mixture was extracted with ethyl acetate (3×50 ml), the combined organic layers washed with brine (50 ml) and dried (MgSO4). The crude product was further purified by crystallization (dichloromethane/MeOH/hexane) to yield the title compound (0.51 g, 63%) as a white solid. MS (ISP) 236.0 [(M−H)−]; mp 151° C.

Workup

  1. customevaporated
  2. additionsaturated NaHCO3 solution (20 ml) was added
  3. extractionThe mixture was extracted with ethyl acetate (3×50 ml)
  4. washthe combined organic layers washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customThe crude product was further purified by crystallization (dichloromethane/MeOH/hexane)

Sources & evidence

ORD record
ord-062209a9e63d47cdba023d6ec6707f84
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

Loading…