Benzene, 1-isocyanato-4-nitro- → HCID 18537658, compound

HRID 412355Notes

Reaction equation

HRID 412355 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([CH2:19][O:20][C:21]4[CH:34]=[CH:33][C:24]([CH2:25][CH:26]5[S:30][C:29](=[O:31])[NH:28][C:27]5=[O:32])=[CH:23][CH:22]=4)[N:16]([CH3:35])[C:15]=3[CH:36]=2)=[CH:4][CH:3]=1.[N+:37]([C:40]1[CH:45]=[CH:44][C:43]([N:46]=[C:47]=[O:48])=[CH:42][CH:41]=1)([O-:39])=[O:38]>CN(C)C=O>[O:31]=[C:29]1[NH:28][C:27](=[O:32])[CH:26]([CH2:25][C:24]2[CH:33]=[CH:34][C:21]([O:20][CH2:19][C:17]3[N:16]([CH3:35])[C:15]4[CH:36]=[C:11]([O:10][CH2:9][CH2:8][C:5]5[CH:6]=[CH:7][C:2]([NH:1][C:47]([NH:46][C:43]6[CH:42]=[CH:41][C:40]([N+:37]([O-:39])=[O:38])=[CH:45][CH:44]=6)=[O:48])=[CH:3][CH:4]=5)[CH:12]=[CH:13][C:14]=4[N:18]=3)=[CH:22][CH:23]=2)[S:30]1

Participants

4

Reactant 2

HCID 66012Benzene, 1-isocyanato-4-nitro-HCID 86587775HCID 86587775, compound

Product 1

HCID 18537658HCID 18537658, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[4-[6-[2-(4-aminophenyl)ethoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (4 g) and N,N-dimethylformamide (10 ml) was added 4-nitrophenyl isocyanate (0.16 g) and the mixture was stirred at room temperature for 1 hour and allowed to stand overnight. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. To the residue was added ethyl acetate. The precipitate was isolated by filtration and purified by preparative normal phase medium pressure liquid chromatography using ethyl acetate:tetrahydrofuran=4:1 as the eluant to give 1-[4-(2-[2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]ethyl)phenyl]-3-(4-nitrophenyl)urea. To a solution of the product in a mixture of tetrahydrofuran and methanol (1:1, 10 ml) was added 4N hydrogen chloride in 1,4-dioxane (2 ml) and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was concentrated and the residue was recrystallized from a mixture of methanol and tetrahydrofuran to afford the title compound (0.16 g, mp 170° C.(dec)).

Workup

  1. waitto stand overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionTo the residue was added ethyl acetate
  7. customThe precipitate was isolated by filtration
  8. custompurified by preparative normal phase medium pressure liquid chromatography

Sources & evidence

ORD record
ord-fce2b76d48614921b6f8c4c73796083d
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

Loading…