Water → HCID 22729266, compound

HRID 2085144Notes

Reaction equation

HRID 2085144 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=O)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:27][C:28]([NH:30][NH2:31])=[O:29].O>C1COCC1>[CH3:1][O:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12]([NH:31][NH:30][C:28](=[O:29])[CH3:27])=[O:14])[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14039AcetohydrazideHCID 682631,1'-CarbonyldiimidazoleHCID 227289824-Methoxy-1-benzofuran-2-carboxylic acid

Product 1

HCID 22729266HCID 22729266, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (700 ml) of 4-methoxybenzo(b)furan-2-carboxylic acid (43.4 g) in THF was added 1,1′-carbonylbis-1H-imidazole (CDI) (38.4 g) and the mixture was stirred at room temperature for 1 hr. Acetohydrazine (17.6 g) was added to this reaction mixture, and the mixture was stirred for 1 more hr. The reaction mixture was poured into water, and the precipitated crystals were collected by filtration and dried to give the title compound (38.4 g) as pale-brown crystals.

Workup

  1. stirringthe mixture was stirred for 1 more hr
  2. filtrationthe precipitated crystals were collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-cd7db74b0fcc48caa2d91ae072005262
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

Loading…