3-(Thien-2-yl)benzoic acid → N-[3-(4,5-dimethylimidazol-1-yl)-phenyl]-3-(2-thienyl)benzamide

HRID 1835480Notes

Reaction equation

HRID 1835480 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O.[CH3:15][C:16]1[N:17]=[CH:18][N:19]([C:22]2[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=2)[NH2:25])[C:20]=1[CH3:21].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:15][C:16]1[N:17]=[CH:18][N:19]([C:22]2[CH:23]=[C:24]([NH:25][C:9](=[O:11])[C:8]3[CH:12]=[CH:13][CH:14]=[C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)[CH:7]=3)[CH:26]=[CH:27][CH:28]=2)[C:20]=1[CH3:21]

Participants

6

Reactant 3

HCID 7368613-(Thien-2-yl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036513-(4,5-Dimethylimidazol-1-yl)phenylamine

Product 1

HCID 23503677N-[3-(4,5-dimethylimidazol-1-yl)-phenyl]-3-(2-thienyl)benzamideYield 62.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 3-(2-thienyl)benzoic acid (103 mg) and 3-(4,5-dimethylimidazol-1-yl)aniline (94 mg) in dichloromethane (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (135 mg) and 4-dimethylaminopyridine (31 mg), and the mixture was stirred for 24 hours. The mixture was diluted with dichloromethane and washed with water and brine. The mixture was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with methanol, and the insoluble material was collected by filtration and dried to give N-[3-(4,5-dimethylimidazol-1-yl)-phenyl]-3-(2-thienyl)benzamide (117 mg, 62.6%).

Workup

  1. washwashed with water and brine
  2. dry with materialThe mixture was dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was triturated with methanol
  5. filtrationthe insoluble material was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-3e926c10f9c94fa28e9370b0c7eea171
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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