m-Chloroperbenzoic acid → HCID 178488145, compound

HRID 1655205Notes

Reaction equation

HRID 1655205 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4]([CH2:9][S:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:13]=3[N:12]=2)[CH:3]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>ClCCl>[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4]([CH2:9][S:10]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:13]=3[N:12]=2)=[O:30])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178488121HCID 178488121, compound

Product 1

HCID 178488145HCID 178488145, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2 -(4 -amino-5 -bromo-2 -pyridylmethylthio)-5 -methoxy-(1H)-benzimidazole (0.58 g, 0.0016 M) was dissolved in dichloromethane (160 ml) and cooled to -40°. m-Chloroperbenzoic acid (0.33 g, 0.0019 M) in dichloromethane (10 ml) was added dropwise over 20 mins, keeping the temperature at 30 ° to -40°. The solution was stirred at -30 ° for 1 hour and then stored at -20 ° overnight, or until reaction was complete. Ammonia was then bubbled through the solution at 50, the mixture allowed to warm up to room temperature, and then filtered. The filtrate and washings were washed with 10 % Na2CO3 (10 ml) an dried. Back extraction of the aqueous layers with dichloromethane (3×100 ml) gave further organic layers which were dried and combined with layers obtained from the first extraction. Evaporation of the combined organic layers gave a brown solid. Purification, by heating in presence of decolouring charcoal in ethyl acetate/methanol, followed by recrystallisation from methanol gave 2 -(4 -amino-5 -bromo-2 -pyridylmethylsulphinyl)-5 -methoxy-(1H)-benzimidazole, 0.21 g, m.p. 130°-132°.

Workup

  1. temperaturecooled to -40°
  2. customat 30 ° to -40°
  3. waitstored at -20 ° overnight
  4. customuntil reaction
  5. customAmmonia was then bubbled through the solution at 50
  6. filtrationfiltered
  7. washThe filtrate and washings were washed with 10 % Na2CO3 (10 ml) an dried
  8. extractionBack extraction of the aqueous layers with dichloromethane (3×100 ml)
  9. customgave further organic layers which
  10. customwere dried
  11. customobtained from the first extraction
  12. customEvaporation of the combined organic layers
  13. customgave a brown solid
  14. customPurification
  15. temperatureby heating in presence of decolouring charcoal in ethyl acetate/methanol
  16. customfollowed by recrystallisation from methanol

Sources & evidence

ORD record
ord-dda6b244289643308437db179c1841de
Source dataset
uspto-grants-1993_10
Patent number
US05250527

Reaction notes

Loading…