Sodium Hydroxide → 4,4'-((4-((3-(4-Morpholinyl)propyl)thio)-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine

HRID 1278338Notes

Reaction equation

HRID 1278338 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1.Cl[C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH2:33][CH2:34][CH2:35][N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)(=[O:32])=[O:31])=[CH:26][C:25]=1[S:42]([CH2:45][CH2:46][CH2:47][N:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1)(=[O:44])=[O:43].Cl.[N:55]1([CH2:61][CH2:62][CH2:63][S:64]C(=N)N)[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1.[OH-].[Na+]>O>[N:55]1([CH2:61][CH2:62][CH2:63][S:64][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH2:33][CH2:34][CH2:35][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)(=[O:32])=[O:31])=[CH:26][C:25]=2[S:42]([CH2:45][CH2:46][CH2:47][N:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)(=[O:44])=[O:43])[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21163758HCID 21163758, compoundHCID 21163760HCID 21163760, compound

Product 1

HCID 211637644,4'-((4-((3-(4-Morpholinyl)propyl)thio)-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.0 g (0.0060 mole) of 4,4'-((4-chloro-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine bis(4-methylbenzenesulfonate), 1.4 g (0.0060 mole) of S-(3-(4-morpholinyl)propyl)isothiourea hydrochloride and 0.8 g (0.02 mole) of sodium hydroxide in 80 ml of water was heated under reflux with stirring for 3.5 hours, cooled and extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation, leaving the product as 4,4'-((4-((3-(4-morpholinyl)propyl)thio)-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine a yellow, viscous oil.

Workup

  1. temperatureunder reflux
  2. temperaturecooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-b4f67c3d4be24bf081206a6bc760a44c
Source dataset
uspto-grants-1981_07
Patent number
US04281118

Reaction notes

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