Sodium Hydroxide → HCID 20333143, compound

HRID 1706941Notes

Reaction equation

HRID 1706941 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18](O)=[O:19])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[Na+].[OH-].[NH4+:29]>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18]([NH2:29])=[O:19])[C:9]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 6472386HCID 6472386, compound

Product 1

HCID 20333143HCID 20333143, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1.55 g. (0.005 mole) of 3-benzyl-2-oxo-1-benzimidazolineacetic acid and 10 ml. of thionyl chloride dissolved in 300 ml. of chloroform is refluxed for a period of approximately 2.5-4 hours. After cooling to room temperature (~25° C.), the reaction mixture is slowly poured into a solution consisting of 4.5 g. of sodium hydroxide dissolved in 100 ml. of ammonium hydroxide. The resulting chloroform layer is then separated and subsequently evaporated to near dryness while under reduced pressure to give a residual solid. Recrystallization of the latter material from ethanol-water then yields pure 3-benzyl-2-oxo-1-benzimidazolineacetamide in fine crystalline form.

Workup

  1. additionA mixture of 1.55 g
  2. additionthe reaction mixture is slowly poured into a solution
  3. customThe resulting chloroform layer is then separated
  4. customsubsequently evaporated
  5. customto give a residual solid
  6. customRecrystallization of the latter material from ethanol-water

Sources & evidence

ORD record
ord-062f9803ea584cd8bde685f2b2c07e32
Source dataset
uspto-grants-1980_06
Patent number
US04209527

Reaction notes

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