Hydrochloric Acid → 3-[3-[(1-Methyl-3-amino-1H-1,2,4-triazol-5-yl)amino]propoxy]benzenemethanol, hydrochloride

HRID 35064Notes

Reaction equation

HRID 35064 reaction equation
[C:1]([N:3]=[C:4]([N:21]([CH3:30])[N:22]=CC1C=CC=CC=1)[NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]2[O:20]CCO2)[CH:11]=1)#[N:2].[ClH:31].C(N(CC)CC)C.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C>[ClH:31].[CH3:30][N:21]1[C:4]([NH:5][CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][OH:20])[CH:13]=[CH:14][CH:15]=2)=[N:3][C:1]([NH2:2])=[N:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 178486227HCID 178486227, compound

Product 1

HCID 1317126873-[3-[(1-Methyl-3-amino-1H-1,2,4-triazol-5-yl)amino]propoxy]benzenemethanol, hydrochloride

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N'-Cyano-N-[3-[3-(1,3-dioxolan-2-yl)phenoxy]propyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidamide (18.2 g) in tetrahydrofuran (150 ml) was treated with 5N hydrochloric acid (30 ml) at 30° C. for 30 mins. Triethylamine (20 ml) was added followed by sodium borohydride (8.0 g). The resulting mixture was stirred at room temperature for 14 hrs, diluted with ethyl acetate (150 ml) and evaporated to a red oil which was dissolved in ethyl acetate, washed with sodium bicarbonate solution and evaporated to leave an oil. This oil was treated with etheral hydrogen chloride to give the title compound as a white solid (8 g). m.p. 148°-9°. TLC silica, ethyl acetate, water, isopropanol 0.88 ammonia (25:8:15:2) Rf 0.56.

Workup

  1. customevaporated to a red oil which
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed with sodium bicarbonate solution
  4. customevaporated
  5. customto leave an oil

Sources & evidence

ORD record
ord-ebcad93417234d96a6e4d773844c10df
Source dataset
uspto-grants-1988_08
Patent number
US04764612

Reaction notes

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