Sodium Hydroxide → HCID 59351215, compound

HRID 887490Notes

Reaction equation

HRID 887490 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[C:18]([C:23]([O:25]CC)=[O:24])=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:14][CH:13]=1)=[O:11].[OH-].[Na+]>CO.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[C:18]([C:23]([OH:25])=[O:24])=[N:19][CH:20]=[CH:21][N:22]=2)=[CH:28][CH:29]=1)=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59351164Ethyl 3-[4-(1H-benzimidazol-2-ylcarbonyl)phenoxy]-2-pyrazinecarboxylate

Product 1

HCID 59351215HCID 59351215, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To the solution of ethyl 3-(4-(1H-benzo[d]imidazole-2 carbonyl)phenoxy)pyrazine-2-carboxylate (30 g, 77 mmol) in methanol (250 mL) was added aqueous NaOH solution (4.62 g, 115 mmol) in 50 mL of water. The reaction mixture was heated to reflux for 1 h. The reaction mixture was concentrated then diluted with water. The aqueous layer was washed with ethyl acetate and then acidified by addition of 2N HCl to pH 6. The precipitate was collected by filtration, dried to give the title compound as a light brown solid. MS [M+H]=351.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. additionthen diluted with water
  5. washThe aqueous layer was washed with ethyl acetate
  6. additionacidified by addition of 2N HCl to pH 6
  7. filtrationThe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-f48f1e02376142598a3bf4288c22bf87
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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