Water → HCID 22460334, compound

HRID 1937276Notes

Reaction equation

HRID 1937276 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(N([CH2:23][CH3:24])CC)C.[C:25](Cl)(=[O:27])[CH3:26].[OH2:29]>C1COCC1>[C:25]([O:17][C:14]1[CH:15]=[CH:16][C:11]([S:10][CH2:9][S:8][C:5]2[CH:4]=[CH:3][C:2]([O:1][C:23](=[O:29])[CH3:24])=[CH:7][CH:6]=2)=[CH:12][CH:13]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 147940714,4'-(Methylenedisulfanediyl)diphenol

Product 1

HCID 22460334HCID 22460334, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 100 g of THF was dissolved 8.8 g (0.038 mol) of the bis (4-hydroxyphenylthio )methane crude product in Synthesis Example 1. 11.5 g (0.11 mol) of triethylamine was added to the solution, which was stirred under ice cooling. 8.9 g (0.11 mol) of acetyl chloride was added dropwise to the solution, which was ripened for one hour in an oil bath at 70° C. After cooling, 26 g of water was added to the solution, which separated into aqueous and organic layers. The organic layer was combined with 100 g of dichloromethane, washed with 100 g of water, and concentrated in vacuum. There was yielded 13 g of an oily residue, which was used in the subsequent reaction without further purification. It is noted that this oily matter crystallized when kept at room temperature.

Workup

  1. customin Synthesis Example 1
  2. temperatureAfter cooling
  3. customseparated into aqueous and organic layers
  4. washwashed with 100 g of water
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1ea1afb6e22d42a3b74b14005c2bbf65
Source dataset
uspto-grants-2002_05
Patent number
US06395446B1

Reaction notes

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