Ammonia → HCID 19824158, compound

HRID 2164281Notes

Reaction equation

HRID 2164281 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:24])([C:16]([C:19](OCC)=[O:20])([CH3:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[NH3:25]>C(O)C>[C:19]([C:16]([CH3:18])([CH3:17])[C:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([OH:24])[CH2:10][N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)(=[O:20])[NH2:25]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19824170HCID 19824170, compound

Product 1

HCID 19824158HCID 19824158, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(2,4-dichlorophenyl)-3-ethoxycarbonyl-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (75 mg) in ethanol (5 ml), aqueous ammonia (sp. gr. 0.88, 12 ml.) was added and the solution was left at room temperature (20° C.) for eight days. The solvent was then evaporated in vacuo, the residue was partitioned between methylene chloride and water, and the organic extracts were washed with brine and dried (MgSO4). Removal of solvent followed by flash chromatography on silica (30 g) and elution with a mixture of methylene chloride/methanol/ammonia (93:7:1) gave the title compound, m.p. 162°-163° C. (34.5 mg).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe residue was partitioned between methylene chloride and water
  3. washthe organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent
  6. washfollowed by flash chromatography on silica (30 g) and elution with a mixture of methylene chloride/methanol/ammonia (93:7:1)

Sources & evidence

ORD record
ord-a4f92950bb8b4bd8982172f023028e07
Source dataset
uspto-grants-1985_03
Patent number
US04503063

Reaction notes

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