Hydrochloric Acid → Zantac

HRID 652569Notes

Reaction equation

HRID 652569 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.O>[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 5039Ranisen

Product 1

HCID 47909Zantac

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

One equivalent (about 5.3 ml) of concentrated hydrochloric acid was added to a solution of ranitidine (20 g) in a mixture of propan-2-ol (130 ml) and water (4 ml) at 45°. The mixture was heated at 50° whilst a further quantity of propan-2-ol (68 ml ) was added and the resulting solution was then stirred at 50° to allow the product to crystallise. The slurry was cooled to 10° to 12° and the product was filtered off, washed with propan-2-ol (2×27 ml) and dried at 50° under reduced pressure to give Form 2 ranitidine hydrochloride (21 g) m.p. 139°-141°.

Workup

  1. additionwas added
  2. customto crystallise
  3. temperatureThe slurry was cooled to 10° to 12°
  4. filtrationthe product was filtered off
  5. washwashed with propan-2-ol (2×27 ml)
  6. customdried at 50° under reduced pressure

Sources & evidence

ORD record
ord-0a14b0a690d74614806279103f85fdd4
Source dataset
uspto-grants-1987_06
Patent number
US04672133

Reaction notes

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