Tetrahydrofuran → 1-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]-2,6-dimethylphenyl)-3-(4-nitrophenyl)urea

HRID 412330Notes

Reaction equation

HRID 412330 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:36]([CH3:37])=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][C:5]=1[CH3:38].[N+:39]([C:42]1[CH:47]=[CH:46][C:45]([N:48]=[C:49]=[O:50])=[CH:44][CH:43]=1)([O-:41])=[O:40].C(N(CC)CC)C.O1CCCC1>CN(C)C=O>[O:29]=[C:27]1[NH:26][C:25](=[O:30])[CH:24]([CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:15]3[N:14]([CH3:33])[C:13]4[CH:34]=[C:9]([O:8][C:7]5[CH:6]=[C:5]([CH3:38])[C:4]([NH:3][C:49]([NH:48][C:45]6[CH:44]=[CH:43][C:42]([N+:39]([O-:41])=[O:40])=[CH:47][CH:46]=6)=[O:50])=[C:36]([CH3:37])[CH:35]=5)[CH:10]=[CH:11][C:12]=4[N:16]=3)=[CH:32][CH:31]=2)[S:28]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 16719220Efatutazone Dihydrochloride

Product 1

HCID 101225001-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]-2,6-dimethylphenyl)-3-(4-nitrophenyl)ureaYield 54.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-[4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione dihydrochloride (288 mg), 4-nitrophenyl isocyanate (98 mg), triethylamine (121 mg), anhydrous tetrahydrofuran (10 ml) and anhydrous N,N-dimethylformamide (10 ml) was stirred at room temperature for 23 hours. The reaction mixture was concentrated and diluted with water. The precipitate was isolated by filtration and then chromatographed on a silica gel column using ethyl acetate as the eluant to afford the title compound (182 mg, mp 178-180° C.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. customThe precipitate was isolated by filtration
  4. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-c37e569f8b4249c7a82621d6ebc3f03d
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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