Sodium Hydroxide → HCID 59351279, compound

HRID 555899Notes

Reaction equation

HRID 555899 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)=[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]([NH:1][CH2:2][CH2:10][C:12]3[CH:29]=[CH:28][CH:15]=[CH:14][CH:13]=3)=[O:25])=[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 59351279HCID 59351279, 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-312b36c46103466dbec065bd06d31f89
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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