3-Fluorobenzyl isocyanate → 2-(2,3-dihydro-1-benzofuran-5-ylcarbonyl)-N-(3-fluorobenzyl)hydrazinecarboxamide

HRID 452601Notes

Reaction equation

HRID 452601 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH2:13])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[F:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[CH2:18][N:19]=[C:20]=[O:21]>N1C=CC=CC=1.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([NH:12][NH:13][C:20]([NH:19][CH2:18][C:17]3[CH:22]=[CH:23][CH:24]=[C:15]([F:14])[CH:16]=3)=[O:21])=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6434993-Fluorobenzyl isocyanateHCID 185264692,3-Dihydro-1-benzofuran-5-carbohydrazide

Product 1

HCID 686644512-(2,3-dihydro-1-benzofuran-5-ylcarbonyl)-N-(3-fluorobenzyl)hydrazinecarboxamideYield 65%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2,3-dihydro-1-benzofuran-5-carbohydrazide (0.50 g, 2.81 mmol) and 3-fluorobenzyl isocyanate (0.85 g, 5.61 mmol) in pyridine (5 mL) was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with ethyl acetate to give the title compound (0.60 g, yield 65%) as colorless crystals.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-70988a3b6cb647c2971100800c3cb15f
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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