Hydrochloric Acid → Zantac

HRID 53909

Reaction equation

HRID 53909 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]([NH:20][CH3:21])=[CH:16][N+:17]([O-:19])=[O:18])=[CH:7][CH:6]=1)[CH3:3].[ClH:22]>C(O)(C)C>[CH3:21][NH:20][C:15]([NH:14][CH2:13][CH2:12][S:11][CH2:10][C:8]1[O:9][C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[CH:6][CH:7]=1)=[CH:16][N+:17]([O-:19])=[O:18].[ClH:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 5039Ranisen

Product 1

HCID 47909Zantac

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-[2-[[[5-(Dimethylamino)methyl-2-furanyl]methyl]thio]ethyl]-N'-methyl-2-nitro-1,1-ethenediamine (100 g) was dissolved in isopropanol (800 ml) containing molar equivalent of hydrogen chloride at 40°-50° C. The solution was stirred further for 1 hr. The hydrochloride crystallized during this period. The product was filtered off, washed with isopropanol twice (100 ml each) and was dried at 40° C. under vacuum to give Form 1 ranitidine hydrochloride (106 g), m.p. 137°-138° C., DSC peak temperature=143.4° C., purity=99.6% (HPLC).

Workup

  1. customThe hydrochloride crystallized during this period
  2. filtrationThe product was filtered off
  3. washwashed with isopropanol twice (100 ml each)
  4. customwas dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-fbb718ef9c3141218cc2c30a9d301eaa
Source dataset
uspto-grants-1997_04
Patent number
US05621120

Linked notes

Loading…