Dichloromethane → HCID 178493213, compound

HRID 2363799Notes

Reaction equation

HRID 2363799 reaction equation
Cl.Cl[CH2:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][N:5]=1.[SH:14][C:15]1[NH:16][C:17]2[CH:23]=[C:22]([O:24][CH:25]([F:27])[F:26])[CH:21]=[CH:20][C:18]=2[N:19]=1.ClCCl.[OH-:31].[Na+:32]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:13][O:12][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:3][S+:14]([O-:31])[C:15]2[N-:19][C:18]3[CH:20]=[CH:21][C:22]([O:24][CH:25]([F:26])[F:27])=[CH:23][C:17]=3[N:16]=2)[C:9]=1[O:10][CH3:11].[Na+:32]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chlorideHCID 178506404HCID 178506404, compound

Product 1

HCID 178493213HCID 178493213, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

2-Chloromethyl-3,4-dimethoxy pyridine hydrochloride (50 gms), 2-mercapto-5-difluoromethoxy benzimidazole (50 gms) and Tetra butyl ammonium bromide (2 gms) were added under stirring to dichloromethane (300 ml) followed by solution of sodium hydroxide (37.5 gms) in 120 ml water. The contents were then stirred at 25-30° C. for about 12 hours. After reaction completion, the dichloromethane layer was separated, then the aqueous layer was extracted with dichloromethane (60 ml) twice. The organic layers were combined together, water washed and distilled to about 250 ml and cooled to 0° C. 3.5% aqueous sodium hypochlorite solution (464 g) having a sodium hydroxide content of 2.2% was added to the reaction mass, which was maintained at 5-8° C. for about 6 hours. After completion of the reaction; the reaction mass was further cooled to 0 to 5° C. The resulting solid was then filtered and washed with cold acetone (about 100 ml) and dried under vacuum at 35-40° C. to give pantoprazole sodium (75 gms, 83%) of purity greater than 99.5%.

Workup

  1. customAfter reaction completion
  2. customthe dichloromethane layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (60 ml) twice
  4. washwater washed
  5. distillationdistilled to about 250 ml
  6. temperaturecooled to 0° C
  7. additionwas added to the reaction mass, which
  8. temperaturewas maintained at 5-8° C. for about 6 hours
  9. customAfter completion of the reaction
  10. temperaturethe reaction mass was further cooled to 0 to 5° C
  11. filtrationThe resulting solid was then filtered
  12. washwashed with cold acetone (about 100 ml)
  13. customdried under vacuum at 35-40° C.

Sources & evidence

ORD record
ord-7dd17bd702c9451e838584a145265e24
Source dataset
uspto-grants-2014_04
Patent number
US08691995B2

Reaction notes

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