Hydrochloric Acid → Zantac

HRID 1247911Notes

Reaction equation

HRID 1247911 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

Procedure

Concentrated hydrochloric acid (1.4 ml) was added to a solution of ranitidine (6 g) in 2-methylpropan-2-ol. The mixture was stirred at 40° to allow the product to crystallise and the resulting slurry was cooled to 20°. Further concentrated hydrochloric acid (about 0.2 ml) was added to the mixture and, after stirring for 1 h at 20° the product was filtered off, washed with 2-methylpropan-2-ol, and dried at 50° under reduced pressure to give Form 2 ranitidine hydrochloride (5.96 g) m.p. 141°-142°.

Workup

  1. customto crystallise
  2. temperaturethe resulting slurry was cooled to 20°
  3. additionFurther concentrated hydrochloric acid (about 0.2 ml) was added to the mixture
  4. stirringafter stirring for 1 h at 20° the product
  5. filtrationwas filtered off
  6. washwashed with 2-methylpropan-2-ol
  7. customdried at 50° under reduced pressure

Sources & evidence

ORD record
ord-e5b4f3621886425392011fb753704a4c
Source dataset
uspto-grants-1985_06
Patent number
US04521431

Reaction notes

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