Dimethylformamide → HCID 21887257, compound

HRID 719802Notes

Reaction equation

HRID 719802 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=O)=[CH:16][C:11]=2[N:10]([CH3:23])[C:9]1=[O:24].CN(C)C=O.[Cl-].[Al+3].[Cl-].[Cl-]>O1CCCC1>[CH3:23][N:10]1[C:11]2[CH:16]=[C:15]3[C:14](=[CH:13][C:12]=2[N:8]([CH3:7])[C:9]1=[O:24])[C:20](=[O:22])[CH2:19][CH2:18][CH2:17]3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 605205HCID 605205, compoundHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21887257HCID 21887257, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (7.0 ml, 81 mmol) was added by portions to a solution of 4-(1,3-dimethyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)butanoic acid (20 g, 81 mmol) obtained in Reference Example 136 and dimethylformamide (1 ml) in tetrahydrofuran under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was concentrated, the reaction residue was dissolved in nitroethane, and aluminum chloride (21.6 g, 162 mmol) was added by portions under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was poured into ice (500 g), extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was crystallized from ethanol-diethyl ether to give the title compound as colorless crystals (18.0 g).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionthe reaction residue was dissolved in nitroethane
  4. temperaturecooling
  5. stirringAfter stirring at room temperature for 30 minutes
  6. extractionextracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customthe residue was crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-fa926753253a4e7babff2d74a1b3582b
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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