Hydrazine → HCID 90031922, compound

HRID 1771268Notes

Reaction equation

HRID 1771268 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15](OCC)=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[NH2:22][NH2:23]>CCO>[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]([NH:22][NH2:23])=[O:16])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 90031234HCID 90031234, compound

Product 1

HCID 90031922HCID 90031922, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 51g (3.73 g, 12.7 mmol, 1.0 equiv.), anhydrous hydrazine (1.6 mL, 50.8 mmol, 4.0 equiv.), EtOH (25 mL, 0.5 M). 46g (2.28 g, 64.1%) was obtained as a white solid after extraction without further purification. 1H-NMR (500 MHz, CDCl3) δ 1H-NMR (500 MHz, CDCl3) δ 8.09 (br s, 1H), 7.37-7.33 (m, 2H), 7.06-7.02 (m, 2H), 3.85 (br s, 2H), 3.70 (br s, 2H), 3.42 (br s, 2H), 3.06 (s, 2H), 2.48 (br s, 4H). 13C-NMR (125 MHz, CDCl3) δ 169.8, 169.5, 163.5 (d, JC-F=249.1 Hz), 131.5 (d, JC-F=2.8 Hz), 129.4 (d, JC-F=9.1 Hz), 115.7 (d, JC-F=22.0 Hz), 60.6, 53.5 (br), 47.7 (br), 42.3 (br). 19F-NMR (470 MHz, CDCl3) δ −113.1. HRMS (ESI): 281.1409 (M+1); calcd. for C13H1sFN4O2: 281.1414.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-6350001dd539422e8abd303b43e561bf
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

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