Sodium hydride → HCID 178513452, compound

HRID 2423245Notes

Reaction equation

HRID 2423245 reaction equation
[H-].[Na+].Cl.[CH:4]([NH2:6])=[NH:5].[F:7][C:8]1[CH:9]=[C:10]([C:15](=[O:38])[C:16](=[C:29]2[NH:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[NH:30]2)[C:17]([C:19]2[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:11]=[C:12]([F:14])[CH:13]=1.[Cl-].[NH4+]>CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([C:15](=[O:38])[C:16](=[C:29]2[NH:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[NH:33]2)[C:17]([C:19]2[CH:20]=[C:21]([S:25]([NH:5][CH:4]=[NH:6])(=[O:26])=[O:27])[CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 1785208713-[3-(3,5-difluorophenyl)-2-(1,3-dihydrobenzimidazol-2-ylidene)-3-oxopropanoyl]benzenesulfonyl chloride

Product 1

HCID 178513452HCID 178513452, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride (809 mg) was added to a DMF (30 mL) solution of formamidine hydrochloride (1.92 g), followed by stirring at room temperature for 15 minutes. A DMF (10 mL) solution of 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]benzenesulfonyl chloride (hereinafter referred to as starting compound A, 1.13 g) was added, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into an excess amount of aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water, concentrated under reduced pressure, purified by silica gel column chromatography (chloroform/methanol=10/1), and crystallized from diethyl ether/n-hexane to obtain 3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]-N-(iminomethyl)benzenesulfonamide (81 mg).

Workup

  1. additionwas added
  2. stirringby stirring at room temperature for 1.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel column chromatography (chloroform/methanol=10/1)
  7. customcrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-2269d2a802044b7d868badbaf0a285a9
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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