Pyridine → HCID 19805162, compound

HRID 1681571Notes

Reaction equation

HRID 1681571 reaction equation
[CH3:1][C:2]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16]([OH:18])=O)([CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[SH:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1.N1C=CC=CC=1>ClCCl>[CH3:12][C:2]([C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[O:22][CH3:23])[C:16]([S:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1)=[O:18])([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 957384-Mercaptobenzoic acidHCID 13633558HCID 13633558, compound2×

Product 1

HCID 19805162HCID 19805162, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 3-(1,1-dimethyldecyl)-4-methoxybenzoic acid, prepared starting with 1.6 g (5 mmoles) of 3-(1,1-dimethyldecyl)-4-methoxybenzoic acid, described in Example 11 of European Patent No. 0.232.199 is dissolved in 20 ml of dichloromethane. The solution is slowly added to a mixture of 771 mg (5 mmoles) of 4-mercaptobenzoic acid and 8 ml of pyridine. The reaction mixture is stirred at ambient temperature for 8 hours, evaporated to dryness, taken up in water, acidified to pH 5 with IN HCl and extracted with ethyl ether (500 ml). The organic phase is decanted, washed with water, dried over magnesium sulfate and evaporated to dryness. The resulting residue is purified by chromatography on a silica column, by using as the eluant ethyl ether. 1.92 g (84% yield) of 4-[3-(1,1-dimethyldecyl)-4-methoxybenzoylthio]benzoic acid whose melting point is 186°-187° C. are obtained.

Workup

  1. customevaporated to dryness
  2. extractionextracted with ethyl ether (500 ml)
  3. customThe organic phase is decanted
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe resulting residue is purified by chromatography on a silica column

Sources & evidence

ORD record
ord-48a7dd001198463a874afa155465fc11
Source dataset
uspto-grants-1992_12
Patent number
US05173289

Reaction notes

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