Sodium borohydride → HCID 12831728, compound

HRID 1706979Notes

Reaction equation

HRID 1706979 reaction equation
[BH4-].[Na+].C[O:4][C:5]([C:7]1[N:11]=[C:10]([CH2:12][N:13]([CH3:15])[CH3:14])[N:9]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]=1)=O>O1CCCC1.CO>[OH:30][CH:23]([C:17]1[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=1[N:9]1[C:10]([CH2:12][N:13]([CH3:14])[CH3:15])=[N:11][C:7]([CH2:5][OH:4])=[N:8]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 12831727HCID 12831727, compound

Product 1

HCID 12831728HCID 12831728, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.1 g (0.24 mole) of sodium borohydride is added portionwise at room temperature, with stirring, to a solution of 16.0 g (0.040 mole) of 1-(2-benzoyl-4-chlorophenyl)-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-carboxylic acid methyl ester [see Example 2] in 320 ml of tetrahydrofuran and 320 ml of methanol. The temperature of the reaction solution rises during the addition to 40°. The reaction mixture is subsequently heated for one hour at 50°; 100 ml of ice water is then added, and the bulk of the tetrahydrofuran and of the methanol is evaporated off in vacuo. The aqueous residue is extracted twice with ethyl acetate. The organic phase is washed once with 1 N sodium hydroxide solution, and is then extracted three times with 2 N hydrochloric acid solution. Sodium carbonate is added to the aqueous acidified extracts until the pH-value reaches 10. The precipitated base is dissolved in ethyl acetate; the solution is washed twice with water and once with saturated sodium chloride solution; it is dried over sodium sulphate and concentrated in vacuo. The residue is triturated with ether and hexane, whereupon the reaction product precipitates in crystalline form. After filtration with suction and drying in vacuum, there is obtained 1-[2-(α-hydroxybenzyl)-4-chlorophenyl]-5-[(dimethylamino)-methyl]-1H-1,2,4-triazole-3-methanol, m.p. 121°-123°.

Workup

  1. additionThe temperature of the reaction solution rises during the addition to 40°
  2. temperatureThe reaction mixture is subsequently heated for one hour at 50°
  3. customthe bulk of the tetrahydrofuran and of the methanol is evaporated off in vacuo
  4. extractionThe aqueous residue is extracted twice with ethyl acetate
  5. washThe organic phase is washed once with 1 N sodium hydroxide solution
  6. extractionis then extracted three times with 2 N hydrochloric acid solution
  7. additionSodium carbonate is added to the
  8. dissolutionThe precipitated base is dissolved in ethyl acetate
  9. washthe solution is washed twice with water and once with saturated sodium chloride solution
  10. dry with materialit is dried over sodium sulphate
  11. concentrationconcentrated in vacuo
  12. customThe residue is triturated with ether and hexane, whereupon the reaction product
  13. customprecipitates in crystalline form
  14. filtrationAfter filtration with suction
  15. customdrying in vacuum

Sources & evidence

ORD record
ord-2987042014e64aa48cbf8ffe7d2f72e2
Source dataset
uspto-grants-1980_06
Patent number
US04209515

Reaction notes

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