Formaldehyde → HCID 68466784, compound

HRID 502986Notes

Reaction equation

HRID 502986 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:23])[C:10]([C:13]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH3:15])[CH3:14])=[N:11][N:12]=1.[CH2:24]=O.S(=O)(=O)(O)O.[BH4-].[Na+].[OH-].[Na+].[Cl-].[Na+]>C(Cl)(Cl)Cl.C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:23])[C:10]([C:13]([N:16]([CH3:24])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([CH3:15])[CH3:14])=[N:11][N:12]=1

Participants

9

Reactant 6

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 68468686HCID 68468686, compound

Product 1

HCID 68466784HCID 68466784, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a THF (7 ml) solution of N-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}aniline (200 mg) were added 36% formaldehyde solution (0.14 ml) and 1.5M sulfuric acid (0.05 ml) and, after stirring at room temperature for 10 minutes, sodium borohydride (81 mg) was added thereto, followed by stirring at room temperature for 10 minutes. After a 1M aqueous sodium hydroxide solution was added to the reaction solution, the reaction solution and chloroform were added to a saturated aqueous sodium chloride solution and then the organic layer was separated. Furthermore, the organic layer was dried over anhydrous magnesium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=99:1) and the resulting solid washed with hexane to obtain 72 mg of N-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}-N-methylaniline (colorless solid).

Workup

  1. stirringby stirring at room temperature for 10 minutes
  2. customthe organic layer was separated
  3. dry with materialFurthermore, the organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=99:1)
  7. washthe resulting solid washed with hexane

Sources & evidence

ORD record
ord-93bcbf4b0c2b4bccb79521ad08994ba0
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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