Water → (E)-N'-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)cyclopropanecarbohydrazide

HRID 587745Notes

Reaction equation

HRID 587745 reaction equation
[F:1][C:2]([F:24])([F:23])[CH:3]([C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[C:16]([Cl:22])[CH:15]=1)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl.[CH:57]1([C:60](Cl)=[O:61])[CH2:59][CH2:58]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:24][C:2]([F:1])([F:23])[CH:3]([C:14]1[CH:15]=[C:16]([Cl:22])[C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=1)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH:13][C:60]([CH:57]2[CH2:59][CH2:58]2)=[O:61])=[CH:8][CH:7]=1

Participants

9

Reactant 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86675193(E)-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)hydrazine

Product 1

HCID 86675211(E)-N'-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)cyclopropanecarbohydrazideYield 55%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of (E)-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)hydrazine (0.1 g, 0.3 mmol) in CH2Cl2 (10 mL) was added DIPEA (65 mg, 0.51 mmol), HOBt.H2O (59 mg, 0.38 mmol), EDC.HCl (73 mg, 0.38 mmol) and cyclopropanecarbonyl chloride (0.024 g, 0.28 mmol), and the reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with satd aq NaHCO3 solution and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (SiO2; 5-25% EtOAc in petroleum ether) afforded the title compound as a solid (65 mg, 55%): mp 138-140° C.; 1H NMR (400 MHz, CDCl3) δ 9.81 (s, 1H), 7.90 (s, 1H), 7.84 (s, 2H), 7.34 (d, J=8.4 Hz, 2H), 6.65 (d, J=15.6 Hz, 1H), 6.61 (m, 1H), 6.57 (s, 1H), 6.48 (dd, J=15.6, 8.8 Hz, 1H), 4.74 (m, 1H), 1.64 (m, 1H), 0.75 (m, 4H); ESIMS m/z 461.32 ([M−H]−).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined CH2Cl2 layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (SiO2; 5-25% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-d792cc2d9b714b3cad29dbe1beb33d94
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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