Hydrazine → HCID 90031337, compound

HRID 1771269Notes

Reaction equation

HRID 1771269 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]([O:18]CC)=O)[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[NH2:25][NH2:26]>CCO>[F:24][C:2]([F:23])([F:1])[C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][C:16]([NH:25][NH2:26])=[O:18])[CH2:13][CH2:14]2)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 90031235HCID 90031235, compound

Product 1

HCID 90031337HCID 90031337, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Synthesized according to General Procedure C: 51i (4.00 g, 11.6 mmol, 1.0 equiv.), anhydrous hydrazine (1.5 mL, 46.4 mmol, 4.0 equiv.), EtOH (25 mL, 0.5 M). 46i (2.35 g, 61.4%) was obtained as a white solid after extraction without further purification. 1H-NMR (500 MHz, CDCl3) δ 8.09 (br s, 1H), 7.62 (d, 2H, J=8.0 Hz), 7.45 (d, 2H, J=8.0 Hz), 3.88 (br s, 2H) 3.75 (br s, 2H), 3.35 (br s, 2H), 3.07 (s, 2H), 2.56 (br s, 2H), 2.42 (br s, 2H). 13C-NMR (125 MHz, CDCl3) δ169.8, 168.9, 139.1 131.8 (q, JC-F=32.1 Hz), 127.5, 125.7 (q, JC-F=3.6 Hz), 123.7 (q, JC-F=271.1 Hz), 60.5, 53.7 (br), 53.2 (br), 47.6 (br), 42.2 (br). 19F-NMR (470 MHz, CDCl3) δ

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-15ae22582f844c4d85070863177a7cc7
Source dataset
uspto-grants-2016_02
Patent number
US09249116B2

Reaction notes

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