Sodium Hydroxide → HCID 178518433, compound

HRID 1281159Notes

Reaction equation

HRID 1281159 reaction equation
[Cl:1][C:2]1[C:37]([Cl:38])=[CH:36][C:5]2[N:6]=[C:7]([C:9]3[N:10](S(C4C=CC(C)=CC=4)(=O)=O)[C:11]4[C:16]([CH:17]=3)=[CH:15][C:14]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:13][CH:12]=4)[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:37]([Cl:38])=[CH:36][C:5]2[N:6]=[C:7]([C:9]3[NH:10][C:11]4[C:16]([CH:17]=3)=[CH:15][C:14]([CH:18]=[C:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:13][CH:12]=4)[NH:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585749HCID 86585749, compound

Product 1

HCID 178518433HCID 178518433, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5,6-dichloro-2-[5-[(2,4-dioxothiazolidin-5-ylidene)methyl]-1-(4-methylphenyl)sulfonylindol-2-yl]benzimidazole (77 mg, 0.13 mmol) in methanol (5 mL) was added aqueous sodium hydroxide (2 mol/L; 1 mL), and the mixture was heated to reflux for 19 h. The reaction mixture was cooled on an ice bath, and pH was adjusted to 7. The precipitated products were collected by filtration followed by trituration with tetrahydrofuran/ethyl acetate to afford 5,6-dichloro-2-[5-[(2,4-dioxothiazolidin-5-ylidene)methyl]indol-2-yl]benzimidazole (10 mg, 18%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 19 h
  3. temperatureThe reaction mixture was cooled on an ice bath
  4. filtrationThe precipitated products were collected by filtration

Sources & evidence

ORD record
ord-a51e7e1f3b7f40b38b206b67cc3080e8
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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