Potassium Carbonate → HCID 16539501, compound

HRID 251032Notes

Reaction equation

HRID 251032 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CCO>[NH:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2[C:18](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]1=[O:26]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 516892Sodium BicarbonateHCID 178527775HCID 178527775, compound

Product 1

HCID 16539501HCID 16539501, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 2-mercaptobenzimidazole (2.0 g, —mmol) and N-(4-bromobutyl)phthalimide (3.8 g, —mmol) in EtOH (50 mL) was added solid K2CO3 (2.2 g, 16 mmol). The resulting mixture was heated to reflux for 18 h, then cooled to room temperature and saturated aqueous NaHCO3 (50 mL) was added. The phases were separated, and the aqueous layer was extracted with CH2Cl2 (3×50 mL) then the combined organic fractions were dried (MgSO4), and concentrated. Purification of the crude material thus obtained by flash chromatography (silica gel, hexane/EtOAc; 4:1) afforded 4.2 g of 2-[4-(1H-benzoimidazol-2-ylsulfanyl)-butyl]-isoindole-1,3-dione (90% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  5. dry with materialthe combined organic fractions were dried (MgSO4)
  6. concentrationconcentrated
  7. customPurification of the crude material
  8. customthus obtained by flash chromatography (silica gel, hexane/EtOAc; 4:1)

Sources & evidence

ORD record
ord-4768e6010afc435a9d61fd9b9d7bebb0
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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