2-Furancarbonyl chloride → HCID 1485419, compound

HRID 2045922Notes

Reaction equation

HRID 2045922 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](Cl)=[O:24]>N1C=CC=CC=1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH:17][C:23]([C:19]2[O:18][CH:22]=[CH:21][CH:20]=2)=[O:24])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 1485419HCID 1485419, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of (3-quinoxalin-2-ylphenyl)amine (2.21 g, 0.01 mol) in pyridine (10 mL) was cooled to 0° C. and 2-furoyl chloride (1 mL, 0.01 mol) was added dropwise over 10 min. The reaction mixture was stirred overnight at room temperature, diluted with water (50 mL), and stirred until precipitate formed. The solid was filtered, dried, and recrystallized from toluene to afford N-[3-(quinoxalin-2-yl)phenyl]furan-2-carboxamide (2.4 g, 76%). LCMS calculated for C19H13N3O2 (M+H): 316.10. found 316. 1H-NMR (DMSO-d6, 250 Mhz) δH: 10.45 (1H, s), 9.51 (1H, s), 8.68 (1H, s), 8.22-7.80 (7H, m), 7.61 (1H, m), 7.40 (1H, m), 6.81 (1H, m).

Workup

  1. stirringstirred until precipitate
  2. customformed
  3. filtrationThe solid was filtered
  4. customdried
  5. customrecrystallized from toluene

Sources & evidence

ORD record
ord-3a4ac4b1207a47d68828d038dfde2d5c
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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