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Calcium Acetate → 2-Acetylbenzofuran-monohydrazone

HRID 321904
Notes
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Reaction equation

HRID 321904 reaction equation
C(C([C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=O)(=O)C.C[N:16](C1C=CC(C=O)=CC=1)C.C([O-])(=O)C.[K+].C([O-])(=O)C.[Ca+2].C([O-])(=O)C.C([O-])(=O)C.[Na+].[C:45](#[N:47])[CH3:46]>C(O)(=O)C.O1CCOCC1.O1CCCC1.CO.C(O)C>[C:45](=[N:47][NH2:16])([C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)[CH3:46]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

12

Reactant 6

HCID 6116Calcium AcetateHCID 6342AcetonitrileHCID 74794-(Dimethylamino)BenzaldehydeHCID 517044Potassium AcetateHCID 517045Sodium AcetateHCID 543109322-Acetylformylbenzofuran

Product 1

HCID 73180426
2-Acetylbenzofuran-monohydrazone

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

In formulae (XVII), (XVIII), (XIX), (XX) and (VII), Ar1, Ar2, Ar3, Ar4, R1, a and n have the same meaning as described above. A 2-acetylformylbenzofuran compound represented by formula (XVII) (1.0 equivalent) and a hydrazine reagent represented by formula (XVIII) (0.95 to 1.00 equivalent) are heated and stirred in an organic solvent, such as ethanol, methanol, tetrahydrofuran, 1,4-dioxane and acetonitrile, to which a catalyst (0.001 to 0.01 equivalent), such as acetic acid, potassium acetate, calcium acetate and sodium acetate, is added, at about 40 to 50° C. for about 3 to 10 hours, so as to obtain a 2-acetylbenzofuran-monohydrazone compound represented by formula (XIX).

Workup

  1. temperatureare heated

Sources & evidence

ORD record
ord-9bdccff19edd4177aaf4aeec32e3c87f
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06210847B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes