Benzoyl chloride → 2,5-Bis(4-benzamidophenyl)furan

HRID 1582712Notes

Reaction equation

HRID 1582712 reaction equation
Cl.Cl.C(NC1C=CC(C2[O:19][C:20]([C:23]3[CH:28]=[CH:27][C:26](NC(=N)C4C=CC=CC=4)=[CH:25][CH:24]=3)=CC=2)=CC=1)(=N)C1C=CC=CC=1.[NH2:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[O:46][C:47]([C:50]3[CH:55]=[CH:54][C:53]([NH2:56])=[CH:52][CH:51]=3)=[CH:48][CH:49]=2)=[CH:41][CH:40]=1.C(N(CC)CC)C.[C:64](Cl)(=[O:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>C(#N)C.O>[C:64]([NH:56][C:53]1[CH:54]=[CH:55][C:50]([C:47]2[O:46][C:45]([C:42]3[CH:43]=[CH:44][C:39]([NH:38][C:20](=[O:19])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:40][CH:41]=3)=[CH:49][CH:48]=2)=[CH:51][CH:52]=1)(=[O:71])[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 120498462,5-Bis(4-aminophenyl)furanHCID 178478770HCID 178478770, compound2×

Product 1

HCID 105826602,5-Bis(4-benzamidophenyl)furanYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2,5-Bis[4-(benzimidoylamino)phenyl]furan Dihydrochloride (Compound 6b) To a chilled solution of 2,5-bis(4-aminophenyl)furan (0.25 g, 1.0 mmol) in dry acetonitrile (10 ml) was added triethylamine (0.22 g, 2.1 mmol) followed dropwise by benzoyl chloride (0.30 g, 2.1 mmol) and the resulting suspension was stirred at room-temperature for 3 hours. Water (10 ml) was then added and the precipitate was collected, rinsed with water, followed by MeOH, and finally dried in vacuo to give 2,5-bis(4-benzamidophenyl)furan as a tan solid (0.44 g, 96%), mp 312-314.5° C. 1H NMR (DMSO-d6): 6.98 (s, 2H), 7.52-7.62 (m, 6H), 7.80 (d, 4H), 7.89 (d, 4H), 7.97 (d, 4H), 10.33 (br s, 2H).

Workup

  1. customthe precipitate was collected
  2. washrinsed with water
  3. customfinally dried in vacuo

Sources & evidence

ORD record
ord-640d511ec0cb49a5b4ba064a42fc2837
Source dataset
uspto-grants-2004_05
Patent number
US06737440B2

Reaction notes

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