m-Chloroperbenzoic acid → HCID 178488147, compound

HRID 1387679Notes

Reaction equation

HRID 1387679 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[N:7]=[C:8]([S:10][CH2:11][C:12]3[C:17]([CH3:18])=[C:16]([O:19][CH3:20])[C:15]([CH3:21])=[CH:14][N:13]=3)[NH:9][C:5]=2[CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:29]>C(OCC)(=O)C>[CH3:21][C:15]1[CH:14]=[N:13][C:12]([CH2:11][S+:10]([O-:29])[C:8]2[NH:7][C:6]3[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=2)=[C:17]([CH3:18])[C:16]=1[O:19][CH3:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 155794Omeprazole sulfide

Product 1

HCID 178488147HCID 178488147, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole (10 g; 0.0304 mole) was suspended in ethyl acetate (100 ml) and cooled below 0° C. 3-chloroperoxybenzoic acid (5.25 g; 0.0304 mole) was added in such a manner that the temperature did not exceed 5° C. After completed addition it was left to crystallize for another half an hour at a temperature below 5° C. The product formed was filtered off, washed with ethyl acetate and dried in vacuo. Crude omeprazole (8.3 g; 79.1%) was obtained.

Workup

  1. temperaturecooled below 0° C
  2. customdid not exceed 5° C
  3. additionaddition it
  4. waitwas left
  5. customto crystallize for another half an hour at a temperature below 5° C
  6. customThe product formed
  7. filtrationwas filtered off
  8. washwashed with ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-df3c730079924b02831193ecbd0b01a5
Source dataset
uspto-grants-2001_07
Patent number
US06268502B1

Reaction notes

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