Sodium borohydride → HCID 42606679, compound

HRID 222377Notes

Reaction equation

HRID 222377 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]([CH:24]=[O:25])=[CH:22][N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+]>C(Cl)Cl.CO>[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]([CH2:24][OH:25])=[CH:22][N:23]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 42605984HCID 42605984, compound

Product 1

HCID 42606679HCID 42606679, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a suspension of 1-[(3,4-dichlorophenyl)methyl]-N-(5-formyl-1,3-thiazol-2-yl)-5-methyl-1H-1,2,3-triazole-4-carboxamide (Example 5) (1.2 g, 30 mmol), in a mixture of DCM/MeOH, was added sodium borohydride (130 mg). The reaction was stirred at room temperature for 1 hour. After evaporation, the residue was poured in a mixture of water/concentrated HCl solution and extracted with ethyl acetate. A solid was formed and filtered. The filtrate was dried over sodium sulphate and evaporated in vacuo. The combined solids were recrystallised from acetonitrile to give the title compound as a yellow solid (0.8 g, 67%). HRMS calculated for C15H13Cl2N5O2S (M+H)+ 398.0245, found: 398.0205, Rt: 2.59 min. MP: 170.5° C.

Workup

  1. customAfter evaporation
  2. additionthe residue was poured in a mixture of water/concentrated HCl solution
  3. extractionextracted with ethyl acetate
  4. customA solid was formed
  5. filtrationfiltered
  6. dry with materialThe filtrate was dried over sodium sulphate
  7. customevaporated in vacuo
  8. customThe combined solids were recrystallised from acetonitrile

Sources & evidence

ORD record
ord-49df11d6d19943acb489c9e01845aa37
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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