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

HRID 1295203Notes

Reaction equation

HRID 1295203 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-c01c5f5b91df478e8ec84cce3aa26b22
Source dataset
uspto-grants-2007_07
Patent number
US07241795B2

Reaction notes

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