Pyridine → 4-[3-(1-Adamantyl)-4-methoxybenzoylthio]benzoic acid

HRID 1681568Notes

Reaction equation

HRID 1681568 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:17]12([C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=3[O:36][CH3:37])[C:30](Cl)=[O:31])[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2>ClCCl>[C:17]12([C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][C:35]=3[O:36][CH3:37])[C:30]([S:1][C:2]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=3)=[O:31])[CH2:18][CH:19]3[CH2:25][CH:23]([CH2:22][CH:21]([CH2:20]3)[CH2:26]1)[CH2:24]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 957384-Mercaptobenzoic acidHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chloride

Product 1

HCID 233627344-[3-(1-Adamantyl)-4-methoxybenzoylthio]benzoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask, there are introduced 1.7 g (11 mmoles) of 4-mercaptobenzoic acid and 20 ml of pyridine. There is then slowly added a solution of 3.4 g (11.17 mmoles) of 3-(1-adamantyl)-4-methoxybenzoic acid chloride in 50 ml of dichloromethane. The reaction mixture is stirred at ambient temperature for 8 hours, evaporated to dryness, taken up in 100 ml of water and acidified to pH 5 with 1N HCl. The solid is filtered, washed with water and dried at 60° C. under a vacuum, then recrystallized in dioxan. 3.3 g (75% yield) of 4-[3-(1-adamantyl)-4-methoxybenzoylthio]benzoic acid having a melting point of 264° C. are obtained.

Workup

  1. customevaporated to dryness
  2. filtrationThe solid is filtered
  3. washwashed with water
  4. customdried at 60° C. under a vacuum
  5. customrecrystallized in dioxan

Sources & evidence

ORD record
ord-b7507f6d817f4ee998e43113a332f6e9
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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