Hydrazine → HCID 64715809, compound

HRID 915687Notes

Reaction equation

HRID 915687 reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>CO.C(OCC)(=O)C>[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH2:12][NH2:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 69130030HCID 69130030, compound

Product 1

HCID 64715809HCID 64715809, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepare a cold (0° C.) solution of 2-(5-phenylthiazol-4-ylmethyl)isoindole-1,3-dione (260 mg, 0.8 mmol) in methanol (15 mL). Add hydrazine (0.05 mL, 1.6 mmol). Warm the reaction to room temperature and stir overnight. Concentrate the reaction in vacuo. Dissolve the residue in ethyl acetate (25 mL) and filter to remove solids. Concentrate the filtrate in vacuo to an oil. Chromatograph (silica gel, 93:6:1 CHCl3/MeOH/concentrated NH4OH) to afford the title compound (130 mg). 1H NMR (CDCl3) δ 8.75 (s, 1H), 7.39-7.49 (m, 5H), 4.00 (s, 2H), 1.62 (br s, 2H).

Workup

  1. temperatureWarm
  2. customthe reaction to room temperature
  3. concentrationConcentrate
  4. customthe reaction in vacuo
  5. filtrationfilter
  6. customto remove solids
  7. concentrationConcentrate the filtrate in vacuo to an oil

Sources & evidence

ORD record
ord-e882b33e42954770a58dd6290e905bc8
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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