Sodium Hydroxide → HCID 42606209, compound

HRID 222373Notes

Reaction equation

HRID 222373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[S:20][C:21]([C:25]([O:27]CC)=[O:26])=[C:22]([CH3:24])[N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[S:20][C:21]([C:25]([OH:27])=[O:26])=[C:22]([CH3:24])[N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 42605981HCID 42605981, compound

Product 1

HCID 42606209HCID 42606209, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 2-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-4-methyl-1,3-thiazole-5-carboxylate (Example 2) (0.482 g, 1.06 mmol) and a 1N NaOH solution (5.5 mL, 5.5 mmol) in ethanol (20 mL) was stirred at 50° C. for 45 min. The reaction was not complete, a 1N NaOH solution (20 mL, 20 mmol) was added and the reaction mixture was stirred for 1 h 30 at 50° C. The solvent was evaporated and the residue was acidified with a 1N HCl solution (25 mL) to pH=1. The precipitate formed was filtered, washed with water and coevaporated with Ethanol. The solid was recrystallised from methanol and washed with DCM to give the title compound as a white solid (418 mg, 92%). HRMS calculated for C16H13Cl2N5O3S (M+H)+426.0194, found: 426.0165, Rt: 2.24 min. MP: 262.6° C.

Workup

  1. customThe solvent was evaporated
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with water
  5. customThe solid was recrystallised from methanol
  6. washwashed with DCM

Sources & evidence

ORD record
ord-bfdac126528c482a853c06a14e51dabe
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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