Sodium Hydroxide → HCID 42606678, compound

HRID 222376Notes

Reaction equation

HRID 222376 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:23][C:22](C(OCC)=O)=[N:21][N:20]=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:23][CH:22]=[N:21][N:20]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 42605982HCID 42605982, compound

Product 1

HCID 42606678HCID 42606678, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3,4-thiadiazole-2-carboxylate (Example 3) (0.302 g, 0.68 mmol) and a 1N NaOH solution (7 mL, 7 mmol) in ethanol (20 mL) was stirred at 50° C. for 1 hour. The solvent was evaporated and the residue was acidified with a 1N HCl solution. The precipitate formed was filtered and the solid was recrystallised from acetonitrile to give the title compound as a white solid (124 mg, 49%). HRMS calculated for C13H10Cl2N6OS (M+H)+369.0092, found: 369.0107, Rt: 2.64 min. MP: 215.6° C.

Workup

  1. customThe solvent was evaporated
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. customthe solid was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-afbd275bd5da4309b215d6d628aaeedc
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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