Hydrochloric Acid → Zantac

HRID 2293631Notes

Reaction equation

HRID 2293631 reaction equation
[ClH:1].[CH3:2][NH:3][C:4]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[O:18][C:17]([CH2:19][N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[CH:5][N+:6]([O-:8])=[O:7]>CC(O)(C)C>[CH3:2][NH:3][C:4]([NH:9][CH2:10][CH2:11][S:12][CH2:13][C:14]1[O:18][C:17]([CH2:19][N:20]([CH3:21])[CH3:22])=[CH:16][CH:15]=1)=[CH:5][N+:6]([O-:8])=[O:7].[ClH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5039Ranisen

Product 1

HCID 47909Zantac

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

Concentrated hydrochloric acid (HCl) (1.4 ml) was added to a solution of ranitidine (6 g) in 2-methylpropan-2-ol. The mixture was stirred at 40° C. to allow the product to crystallize and the resultant slurry was cooled to 20° C. Further concentrated HCl (about 0.2 ml) was added to the mixture and stirred for one hour at 20° C. 0.04 g pyridine was added to the reaction mixture. The product was filtered off, washed with 2-methylpropan-2-ol and dried at 50° C. under reduced pressure to give 5.96 g of Form II ranitidine hydrochloride having a melting point of 141°-142° C.

Workup

  1. customto crystallize
  2. temperaturethe resultant slurry was cooled to 20° C
  3. additionFurther concentrated HCl (about 0.2 ml) was added to the mixture
  4. stirringstirred for one hour at 20° C
  5. addition0.04 g pyridine was added to the reaction mixture
  6. filtrationThe product was filtered off
  7. washwashed with 2-methylpropan-2-ol
  8. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-33fa246bfecf45328443ccfe53419156
Source dataset
uspto-grants-1997_11
Patent number
US05686588

Reaction notes

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