Pyridine → HCID 178504394, compound

HRID 1681574Notes

Reaction equation

HRID 1681574 reaction equation
[C:1]12([C:11]3[C:12]([O:24][SiH:25]([CH3:27])[CH3:26])=[C:13]([CH:17]=[CH:18][C:19]=3[C:20]([CH3:23])([CH3:22])[CH3:21])[C:14](O)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[SH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=1.N1C=CC=CC=1>ClCCl>[C:1]12([C:11]3[C:12]([O:24][SiH:25]([CH3:27])[CH3:26])=[C:13]([CH:17]=[CH:18][C:19]=3[C:20]([CH3:21])([CH3:22])[CH3:23])[C:14]([S:28][C:29]3[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=3)=[O:15])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 957384-Mercaptobenzoic acidHCID 137327945HCID 137327945, compound

Product 1

HCID 178504394HCID 178504394, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 3-(1-adamantyl)-4-tert.butyl-dimethylsilyloxybenzoic acid, prepared starting with 3.8 g (9.95 mmoles) of the corresponding acid, described in Example 3 of European Patent No. 0.232.199, is dissolved in 40 ml of dichloromethane. The solution is slowly added to a mixture of 1.54 g (9.95 mmoles) of 4-mercaptobenzoic acid and 15 ml of pyridine. The reaction mixture is stirred at ambient temperature for 12 hours, evaporated to dryness, taken up in water and acidified to pH 5 with 1N HCl. The solid is filtered, washed with water, ground with 50 ml of ethyl ether and dried at 60° C. under a vacuum. 5 g (96% yield) of a white powder whose melting point is 232°-233° C. are recovered.

Workup

  1. customevaporated to dryness
  2. filtrationThe solid is filtered
  3. washwashed with water, ground with 50 ml of ethyl ether
  4. customdried at 60° C. under a vacuum

Sources & evidence

ORD record
ord-02b80572e7fc4385be033e27650cdc27
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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