Water → HCID 178501896, compound

HRID 230736

Reaction equation

HRID 230736 reaction equation
S(OS([O-])=O)([O-])=O.[Na+].[Na+].[Cl:10][C:11]1[S:12][C:13]([CH:16]=O)=[CH:14][CH:15]=1.[NH2:18][C:19]1[CH:20]=[C:21]([S:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1[NH2:25].O>CN1CCCC1=O>[Cl:10][C:11]1[S:12][C:13]([C:16]2[NH:25][C:24]3[CH:23]=[CH:22][C:21]([S:26]([CH2:29][C:30]([O:32][CH3:33])=[O:31])(=[O:28])=[O:27])=[CH:20][C:19]=3[N:18]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24346Disodium disulfiteHCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 57763314Methyl (3,4-diaminobenzenesulfonyl)acetate

Product 1

HCID 178501896HCID 178501896, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

14.4 747 mg (3.93 mmol) of sodium disulfite are added to a solution of 1.15 g (7.86 mmol) of 2-chlorothiophene-5-carbaldehyde and 1.92 g (7.86 mmol) of methyl (3,4-diaminobenzenesulfonyl)acetate in 25 ml of 1-methylpyrrolidone, and the mixture is stirred at 110° C. for 18 hours. Water is added to the reaction mixture, which is extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is stirred with water, and the resultant precipitate is filtered off, giving methyl [2-(5-chlorothiophen-2-yl)-1H-benzimidazole-5-sulfonyl]-acetate as a brown solid; ESI 371.

Workup

  1. extractionis extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated
  4. stirringThe residue is stirred with water
  5. filtrationthe resultant precipitate is filtered off

Sources & evidence

ORD record
ord-f5de34153b9b43da8657d33176101420
Source dataset
uspto-grants-2009_07
Patent number
US07566789B2

Linked notes

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