Sodium Hydroxide → 5-(3-Imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine

HRID 1092985Notes

Reaction equation

HRID 1092985 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:16]3[S:20][C:19]([NH:21]C(=O)C)=[N:18][C:17]=3[CH3:25])[CH:9]=[CH:10][C:11]=2[S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+]>C(O)C.Cl>[N:1]1([C:6]2[CH:7]=[C:8]([C:16]3[S:20][C:19]([NH2:21])=[N:18][C:17]=3[CH3:25])[CH:9]=[CH:10][C:11]=2[S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53429448Acetamide, N-[5-[3-(1H-imidazol-1-YL)-4-(methylsulfonyl)phenyl]-4-methyl-2-thiazolyl]-

Product 1

HCID 574737535-(3-Imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-ylamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A stirred solution of N-[5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 80) (0.80 g, 2.13 mmol) in ethanol (15 ml) and 7M aqueous HCl (20 ml) is heated at 90° C. for 2 hours. The solution is allowed to cool, brought to pH 10 by addition of aqueous NaOH and extracted with n-butanol. The organic extract is dried (MgSO4), the solvent is removed and the residue is triturated with ethanol to give the titled compound as a yellow solid.

Workup

  1. temperatureto cool
  2. extractionextracted with n-butanol
  3. extractionThe organic extract
  4. dry with materialis dried (MgSO4)
  5. customthe solvent is removed
  6. customthe residue is triturated with ethanol

Sources & evidence

ORD record
ord-14a89c07a1ce4f48a1815a3fb501bf7a
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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