3-Chlorobenzoic Acid → HCID 131724218, compound

HRID 480680Notes

Reaction equation

HRID 480680 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([S@:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[C:17](C)=[CH:16][N:15]=3)=[O:12])[NH:8][C:7]=2[CH:24]=1.Cl[C:26]1C=C(C=CC=1)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([S@:11]([CH2:13][C:14]3[C:19]([CH3:20])=[C:18]([O:21][CH3:22])[CH:17]=[C:16]([CH3:26])[N:15]=3)=[O:12])[NH:8][C:7]=2[CH:24]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 14798Sodium HydroxideHCID 9568614Esomeprazole

Product 1

HCID 131724218HCID 131724218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(5)6-methoxy-2[[(4methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]1H-benzimidazole (16.2 g; 0.0492 mol)) is reacted with m-chlorobenzoic acid (13.6 g; 0.0537 mol) with CH2Cl2 acting as a solvent at a pH of 8.6. The pH is maintained by the presence of KHCO3 (5.6 g; 0.056 mol) acting as a buffer. The temperature is maintained at about 0° C. during the addition. Diluted NaOH is added to a pH above 12 and the CH2Cl2 phase is separated off. Dimethylformamide (4.7 g) is charged to the water phase and the pH is kept above 9, whereupon crystals a mixture of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole are formed. The crystals are filtered off and are washed with water and methanol at a temperature of about 0° C. The washed crystals are then dried under vacuum and are found to predominantly contain 6-methoxy-2-[[(4-methoxy-3,5dimethyl-2-pyridinyl)methyl]sulfinyl]1H-benzimidazole.

Workup

  1. customthe CH2Cl2 phase is separated off
  2. additionDimethylformamide (4.7 g) is charged to the water phase
  3. additiona mixture of (5)6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
  4. customare formed
  5. filtrationThe crystals are filtered off
  6. washare washed with water and methanol at a temperature of about 0° C
  7. customThe washed crystals are then dried under vacuum

Sources & evidence

ORD record
ord-9f31a8da0f2044b783865c11cd4cba34
Source dataset
uspto-grants-2003_11
Patent number
US06653329B1

Reaction notes

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