HCID 4585939, compound → HCID 23347027, compound

HRID 1855937Notes

Reaction equation

HRID 1855937 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]#[N:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:17][O-:18].[Na+]>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15](=[NH:16])[O:18][CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4585939HCID 4585939, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 23347027HCID 23347027, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 10.7 (0.05 ml) of 5-(4-nitrophenyl)-2-furonitrile and 500 ml of anhydrous methanol was heated on a steam bath until a solution resulted. After slight cooling, a catalytic amount (0.1 g) of powdered sodium methoxide was added with stirring. The solution turned quite dark and in about 5 minutes, solid started to separate. The mixture was allowed to stir for an hour and then was filtered. The solid was washed with anhydrous methanol and air dried. The yield was 10.0 g (81%). Recrystallization from 200 ml of ethyl acetate gave 6.0 g of analytically pure methyl 5-(4-nitrophenyl)-2-furancarboximidate, m.p. 184°-188°.

Workup

  1. temperaturewas heated on a steam bath until a solution
  2. customresulted
  3. customto separate
  4. stirringto stir for an hour
  5. filtrationwas filtered
  6. washThe solid was washed with anhydrous methanol and air
  7. customdried
  8. customRecrystallization from 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-ca879d2f155f4e98af38f44c23c70482
Source dataset
uspto-grants-1980_08
Patent number
US04217286

Reaction notes

Loading…