Water → HCID 117988387, compound

HRID 710944Notes

Reaction equation

HRID 710944 reaction equation
[NH:1]([C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])[NH2:2].O.C(=O)([O-])O.[Na+].[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](Cl)=[O:25]>O1CCCC1.C(OCC)(=O)C>[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24]([NH:2][NH:1][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 682422-Furancarbonyl chlorideHCID 79242Benzyl carbazateHCID 516892Sodium Bicarbonate

Product 1

HCID 117988387HCID 117988387, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl hydrazinecarboxylate (1.66 g, 10.0 mmol) was dissolved in tetrahydrofuran (20 mL) and water (20 mL) and added sodium hydrogen carbonate (1.68 g) thereto. Under ice cooling, furan-2-carbonyl chloride (1.30 g, 10 mmol) was gradually added, followed by stirring for 1 hour. After completion of the reaction, to the reaction solution was added 300 ml of ethyl acetate, followed by washing with saturated ammonium chloride solution and saturated brine. The organic layer was dried over magnesium sulfate, the solvent was distilled off under reduced pressure, and 5 ml of ethyl acetate was dissolved in the resulting residue, followed by gradually adding hexane (100 ml) to afford 2.30 g of the title compound as a solid (yield 88.4%).

Workup

  1. customAfter completion of the reaction
  2. washby washing with saturated ammonium chloride solution and saturated brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure, and 5 ml of ethyl acetate
  5. dissolutionwas dissolved in the resulting residue

Sources & evidence

ORD record
ord-2e621a0a79a742048b3645e823fc59a7
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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