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

HRID 19710Notes

Reaction equation

HRID 19710 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-9168817f33114f3f8b240fcfc9b366a4
Source dataset
uspto-grants-2010_06
Patent number
US07745456B2

Reaction notes

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