Ethanolamine → 5-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-N-(2-hydroxy-ethyl)-2-methoxy-benzenesulfonamide

HRID 2247332Notes

Reaction equation

HRID 2247332 reaction equation
[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[S:7][C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18](Cl)(=[O:20])=[O:19])[CH:17]=2)=[C:9]([CH3:11])[N:10]=1)[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[CH2:31]([CH2:33][NH2:34])[OH:32].O>O1CCOCC1.C(Cl)Cl.CO.C(OC(=O)C)C>[CH2:1]([NH:3][C:4](=[O:24])[NH:5][C:6]1[S:7][C:8]([C:12]2[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18]([NH:34][CH2:33][CH2:31][OH:32])(=[O:20])=[O:19])[CH:17]=2)=[C:9]([CH3:11])[N:10]=1)[CH3:2]

Participants

8

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 10340Sodium CarbonateHCID 865984045-[2-(3-Ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy benzenesulfonylchloride

Product 1

HCID 865984065-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-N-(2-hydroxy-ethyl)-2-methoxy-benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To 5-[2-(3-Ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy benzenesulfonylchloride (Example 28d) (0.2 g, 0.514 mmol) in dioxane (10 ml) is added 2M Na2CO3 (0.515 ml) followed by ethanolamine (0.031 ml, 0.514 mmol). After 2 hours at room temperature, the reaction mixture is poured into water (150 ml)/ethylacetate (50 ml) and sonicated. The layers are separated then the aqueous layer is extracted with ethyl acetate (3×50 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to afford a sticky oil which is dissolved in a minimum amount of DCM/methanol and dried at reduced pressure to afford 5-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-N-(2-hydroxy-ethyl)-2-methoxy-benzenesulfonamide as a yellow foam.

Workup

  1. customsonicated
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with ethyl acetate (3×50 ml)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a sticky oil which
  8. customdried at reduced pressure

Sources & evidence

ORD record
ord-7be961f06ddb418eab7ab95e5f11ca65
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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