Sodium borohydride → HCID 54158435, compound

HRID 2058722Notes

Reaction equation

HRID 2058722 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]([CH3:21])[CH3:20])[CH:13]=2)=[N:5][C:4]([N:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:3]1.[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][N:19]([CH3:20])[CH3:21])[CH:13]=2)=[N:5][C:4]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 544958511-Methyl-N3-phenylmethylene-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine

Product 1

HCID 54158435HCID 54158435, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-N3 -phenylmethylene-N5 -[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (2.0 g) and sodium borohydride (0.95 g) in methanol was stirred at 25° for 12 hr. The mixture was poured onto water and extracted with ethyl acetate. The organic extract was washed with ethyl acetate. The organic extract was washed with brine and distilled to give the title compound as a pale yellow oil (1.4 g) b.p. 180° (0.04 mm). TLC silica; methanol:ammonia (80:1) Rf 0.7.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. distillationdistilled

Sources & evidence

ORD record
ord-6e68d88cca064d15a30bf4ca6452ce78
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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