Hydrazine → 4-(Octyloxy)-3-(trifluoromethyl)benzohydrazide

HRID 2357063Notes

Reaction equation

HRID 2357063 reaction equation
[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CN(C(O[N:31]1[N:39]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.NN>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH:31][NH2:39])=[O:15])=[CH:12][C:11]=1[C:19]([F:22])([F:21])[F:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 533492554-Octyloxy-3-trifluoromethylbenzoic acid

Product 1

HCID 533493604-(Octyloxy)-3-(trifluoromethyl)benzohydrazideYield 105.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

4-(Octyloxy)-3-(trifluoromethyl)benzoic acid (11a) (632 mg, crude, approximately 1.89 mmol) was stirred with HATU (905 mg) and DIEA (1.7 mL) in CH2Cl2-DMF (10 mL, 4:1) for 10 min followed by addition of hydrazine (297 μL) dropwise. The reaction mixture was continuously stirred for another hour, then was diluted with ethyl acetate (30 mL) and washed with water (10 mL) and brine (3×15 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound (661 mg, HPLC purity >90%), which was used for next reaction without further purification. MS (ESI): 333.08 (MH+); HPLC retention time on a C8(2) column (30×3.00 mm, 3μ) is 1.61 min with gradient 50-98% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase.

Workup

  1. washwashed with water (10 mL) and brine (3×15 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56b50cc8ab754905b829b59d7c0d9932
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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