Zantac → Ranitidine docusate

HRID 1517229Notes

Reaction equation

HRID 1517229 reaction equation
[CH3:1][NH:2][C:3]([NH:8][CH2:9][CH2:10][S:11][CH2:12][C:13]1[O:17][C:16]([CH2:18][N:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=[CH:4][N+:5]([O-:7])=[O:6].Cl.[Na].[CH3:24][CH2:25][CH2:26][CH2:27][CH:28]([CH2:31][O:32][C:33]([CH2:35][CH:36]([S:48]([OH:51])(=[O:50])=[O:49])[C:37]([O:39][CH2:40][CH:41]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:42][CH3:43])=[O:38])=[O:34])[CH2:29][CH3:30]>O>[CH3:1][NH:2][C:3]([NH:8][CH2:9][CH2:10][S:11][CH2:12][C:13]1[O:17][C:16]([CH2:18][N:19]([CH3:20])[CH3:21])=[CH:15][CH:14]=1)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:24][CH2:25][CH2:26][CH2:27][CH:28]([CH2:31][O:32][C:33]([CH2:35][CH:36]([S:48]([OH:51])(=[O:50])=[O:49])[C:37]([O:39][CH2:40][CH:41]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:42][CH3:43])=[O:38])=[O:34])[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 47909ZantacHCID 9955175Sodium docusate2×

Product 1

HCID 86612077Ranitidine docusate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

In a reaction vessel charged with a magnetic stirbar, 2.50 g (7.12 mmol) of Ranitidine hydrochloride was dissolved in approximately 25 mL of deionized water. In a separate reaction vessel, similarly charged with a stirbar, 3.17 g (7.12 mmol) of sodium docusate was dissolved/suspended in 25 mL of warm, deionized water. To the latter solution was added in one portion the aqueous solution of sodium docusate. The deep orange-brown milieu was stirred overnight, after which time the aqueous system was repeatedly extracted with 100 mL portions of chloroform. Emulsification of the two phases was quite pronounced, so each time the system was heated to about 60 ° C., then allowed to cool and settle for 5-7 days, after which point the dark chloroform phase was separated, dried over anhydrous MgSO4, filtered, and rotary evaporated to yield a viscous, deep brown-orange oil (Ranitidine docusate). The two ions have known histamine H2-receptor antagonist and an emollient properties, respectively.

Workup

  1. customIn a separate reaction vessel
  2. temperatureof warm
  3. extractionafter which time the aqueous system was repeatedly extracted with 100 mL portions of chloroform
  4. temperatureto cool
  5. waitsettle for 5-7 days
  6. customafter which point the dark chloroform phase was separated
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customrotary evaporated

Sources & evidence

ORD record
ord-026e434cc59549f7a12f47eb03522313
Source dataset
uspto-grants-2012_07
Patent number
US08232265B2

Reaction notes

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