Ammonia → 5-[2-(3-Ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy-benzenesulfonamide

HRID 2247331Notes

Reaction equation

HRID 2247331 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+].[NH3:31].O>O1CCOCC1>[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]([NH2:31])(=[O:20])=[O:19])[CH:17]=2)=[C:9]([CH3:11])[N:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 10340Sodium CarbonateHCID 865984045-[2-(3-Ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy benzenesulfonylchloride

Product 1

HCID 865984055-[2-(3-Ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of 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 2 M Na2CO3 (0.515 ml) followed by 0.5 M NH3 in dioxane (2.06 ml). After 2 hours at room temperature, the reaction mixture is poured into water (200 ml) then extracted with ethyl acetate (3×50 ml). The combined organic layers are dried over MgSO4, filtered and concentrated to afford 5-[2-(3-ethyl-ureido)-4-methyl-thiazol-5-yl]-2-methoxy-benzenesulfonamide as a yellow powder.

Workup

  1. extractionthen extracted with ethyl acetate (3×50 ml)
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ef37060d6aeb431f833b74c42a77cb8d
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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