Hydrochloric Acid → HCID 178518432, compound

HRID 1281160Notes

Reaction equation

HRID 1281160 reaction equation
[Cl:1][C:2]1[C:37]([Cl:38])=[CH:36][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[N:14](S(C3C=CC(C)=CC=3)(=O)=O)[C:13]([CH:28]=[C:29]3[S:33][C:32](=[O:34])[NH:31][C:30]3=[O:35])=[CH:12]4)[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl>CO.CN(C)C=O.O>[Cl:1][C:2]1[C:37]([Cl:38])=[CH:36][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]4[C:15](=[CH:16][CH:17]=3)[NH:14][C:13]([CH:28]=[C:29]3[S:33][C:32](=[O:34])[NH:31][C:30]3=[O:35])=[CH:12]4)[NH:8][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 86585750HCID 86585750, compound

Product 1

HCID 178518432HCID 178518432, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5,6-dichloro-2-[2-[(2,4-dioxothiazolidin-5-ylidene)methyl]-1-(4-methylphenyl)sulfonylindol-5-yl]benzimidazole (100 mg, 0.172 mmol) in methanol (7.5 mL) was added aqueous sodium hydroxide (2 mol/L; 1.5 mL), and the mixture was heated to reflux for 3.5 h. The reaction mixture was cooled on an ice bath, and pH was adjusted to 7. The precipitated products were collected by filtration, washed with water, and dried. To a solution of the product (50 mg) in dimethylformamide (2 mL) was added 1,1′-carbonyldiimidazole (15 mg, 0.12 mmol), and the mixture was stirred at room temperature for 30 min. Hydrochloric acid (1 mol/L; 0.5 mL) and water were added to the mixture, and the precipitated product was filtered off and washed with water and ethanol to afford 5,6-dichloro-2-[2-[(2,4-dioxothiazolidin-5-ylidene)methyl]indol-5-yl]benzimidazole (18 mg, 24%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3.5 h
  3. temperatureThe reaction mixture was cooled on an ice bath
  4. filtrationThe precipitated products were collected by filtration
  5. washwashed with water
  6. customdried
  7. filtrationthe precipitated product was filtered off
  8. washwashed with water and ethanol

Sources & evidence

ORD record
ord-853da64da0484a41a3e194a2f3b3b7a2
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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