Sodium Carbonate → N-(3-Bromo-4-chlorophenyl)-3-furancarboxamide

HRID 2114153Notes

Reaction equation

HRID 2114153 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[O:10]1[CH:14]=[CH:13][C:12]([C:15](Cl)=[O:16])=[CH:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:15]([C:12]2[CH:13]=[CH:14][O:10][CH:11]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27761233-Furoyl chlorideHCID 128437223-Bromo-4-chloroaniline

Product 1

HCID 69204621N-(3-Bromo-4-chlorophenyl)-3-furancarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Bromo-4-chloroaniline (150 mg), 3-furoylchloride (0.15 ml) and sodium carbonate (1 g) were stirred for 18 hours at room temperature in DCM (15 ml). The reaction was filtered, the residue washed with DCM and the combined DCM fractions reduced to dryness under vacuum to give N-(3-bromo-4-chlorophenyl)-3-furamide. NMR; δH [2H6]—DMSO 10.13,(1H, s), 8.38,(1H, s), 8.20,(1H, d), 7.81,(1H, m), 7.73,(1H, dd), 7.59,(1H, d), 6.97,(1H, m).

Workup

  1. filtrationThe reaction was filtered
  2. washthe residue washed with DCM

Sources & evidence

ORD record
ord-0ea065d2a5a042f8a27f6bb044c5fae8
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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