Triethylamine → 2,2,2-Triphenylacetohydrazide

HRID 349169Notes

Reaction equation

HRID 349169 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.C(N(CC)CC)C.O.[NH2:46][NH2:47]>CN(C)C=O.O>[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([NH:46][NH2:47])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 68992Triphenylacetic acidHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphate

Product 1

HCID 153699862,2,2-TriphenylacetohydrazideYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylacetic acid (499.6 mg, 1.73 mmol) was dissolved in N,N-dimethylformamide (DMF, 3.46 mL). Fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (TFFH, 460.1 mg, 1.742 mmol) and anhydrous triethylamine (480 μl, 3.44 mmol) were added and the solution was cooled to 0° C. After 10 minutes hydrazine monohydrate (168 μl, 3.46 mmol) was added. The reaction was allowed to warm, and after stirring at room temperature for 30 minutes, it was worked up by adding water and filtering the resulting precipitate. The precipitate was dried under vacuum to give 2,2,2-triphenylacetohydrazide (340.1 mg).

Workup

  1. temperatureto warm
  2. filtrationfiltering the resulting precipitate
  3. customThe precipitate was dried under vacuum

Sources & evidence

ORD record
ord-0e9c49cf87154fe1b840c06a4595de6a
Source dataset
uspto-grants-2007_02
Patent number
US07179802B2

Reaction notes

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