4-Methylbenzenethiol → 4,4'-((4-((4-Methylphenyl)thio)-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine bis(4-methylbenzenesulfonate)

HRID 1278337Notes

Reaction equation

HRID 1278337 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:15][CH:14]=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].[CH3:54][C:55]1[CH:60]=[CH:59][C:58]([SH:61])=[CH:57][CH:56]=1.[OH-].[Na+]>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:17][CH:18]=1.[CH3:54][C:55]1[CH:60]=[CH:59][C:58]([S:61][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])=[CH:57][CH:56]=1

Participants

5

Reactant 3

HCID 78114-MethylbenzenethiolHCID 14798Sodium HydroxideHCID 21163758HCID 21163758, compound

Product 1

HCID 211637594,4'-((4-((4-Methylphenyl)thio)-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine bis(4-methylbenzenesulfonate)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 10.0 g (0.0119 mole) of 4,4'-((4-chloro-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine bis(4-methylbenzenesulfonate), 1.6 g (0.012 mole) of 90% p-thiocresol and 1.5 g (0.038 mole) of sodium hydroxide in 55 ml of water was warmed for 30 minutes at 65° to 70° C., during which time the crude product separated as a hard gum. The aqueous phase was decanted, and the gum was dissolved in a minimum of warm propanol-2. This solution was treated with a propanol-2 solution of an excess of p-toluenesulfonic acid monohydrate. On cooling, the solution yielded a crystalline product. Recrystallization from propanol-2 gave the pure product, 4,4'-((4-((4-methylphenyl)thio)-1,3-phenylene)bis(sulfonyl-3,1-propanediyl))bismorpholine bis(4-methylbenzenesulfonate), as buff crystals, m.p. 215.5°-216.5° C.

Workup

  1. customseparated as a hard gum
  2. customThe aqueous phase was decanted
  3. dissolutionthe gum was dissolved in a minimum of warm propanol-2
  4. additionThis solution was treated with a propanol-2 solution of an excess of p-toluenesulfonic acid monohydrate
  5. temperatureOn cooling
  6. customthe solution yielded a crystalline product
  7. customRecrystallization from propanol-2

Sources & evidence

ORD record
ord-66c4941ca71b4a0680fd7b8fced9fd4c
Source dataset
uspto-grants-1981_07
Patent number
US04281118

Reaction notes

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