Hydrazine hydrate (1:1) → HCID 59525774, compound

HRID 385746Notes

Reaction equation

HRID 385746 reaction equation
[N+:1]([C:4]1[S:5][C:6]([C:12]2[N:16]=[CH:15][N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:13]=2)=[CH:7][C:8]=1[C:9]([NH2:11])=[O:10])([O-])=O.O.NN>CO>[NH2:1][C:4]1[S:5][C:6]([C:12]2[N:16]=[CH:15][N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[N:13]=2)=[CH:7][C:8]=1[C:9]([NH2:11])=[O:10]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59525948HCID 59525948, compound

Product 1

HCID 59525774HCID 59525774, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 2-nitro-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)thiophene-3-carboxamide (600 mg, 1.62 mmol) in MeOH (25 mL) was added FeCl3 (13 mg, 0.081 mmol). The solution was heated to reflux, and hydrazine hydrate (65%, 0.364 ml, 4.87 mmol) was added. After stirring for 30 minutes at reflux, the mixture was cooled to room temperature, combined with MeOH and silica gel, and evaporated to dryness. Flash chromatography (dry load, 0-10% MeOH/EtOAc) afforded the title compound as a colorless solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. temperatureat reflux
  4. customevaporated to dryness
  5. dry with materialFlash chromatography (dry load, 0-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-45beb1e9d6964b9d8f9a8a238dafe241
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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