4-Mercaptobenzoic acid → HCID 88299401, compound

HRID 1417752Notes

Reaction equation

HRID 1417752 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]12([C:21]3[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2>N1C=CC=CC=1>[C:11]12([C:21]3[CH:29]=[CH:28][C:24]([C:25]([S:1][C:2]4[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=4)=[O:26])=[CH:23][C:22]=3[O:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[CH2:12][CH:13]3[CH2:14][CH:15]([CH2:16][CH:17]([CH2:19]3)[CH2:18]1)[CH2:20]2

Participants

4

Reactant 2

HCID 957384-Mercaptobenzoic acidHCID 57185006HCID 57185006, compound

Product 1

HCID 88299401HCID 88299401, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

850 mg (5.5 mmol) of 4-mercaptobenzoic acid and 20 ml of pyridine were introduced into a round-bottomed flask. A solution of 2.08 g (5.5 mmol) of 4-(1-adamantyl)-3-methoxyethoxymethoxybenzoyl chloride prepared above was added dropwise and the mixture was stirred at room temperature for six hours. It was evaporated to dryness and the residue was taken up in water and ethyl acetate and acidified to pH 5, and the organic phase was separated out after settling had taken place, washed with water, dried over magnesium sulfate and evaporated. The solid obtained was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and methanol (98/2). 1.5 g (57%) of 4-[4-(1-adamantyl)-3-methoxyethoxymethoxybenzoylthio]benzoic acid, having a melting point of 219°-21° C., was recovered.

Workup

  1. additionabove was added dropwise
  2. customIt was evaporated to dryness
  3. customthe organic phase was separated out
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe solid obtained
  8. customwas purified by chromatography on a column of silica
  9. washeluted with a mixture of dichloromethane and methanol (98/2)
  10. customwas recovered

Sources & evidence

ORD record
ord-4f544a94e14d463ca499f53daa344eef
Source dataset
uspto-grants-1999_03
Patent number
US05877342

Reaction notes

Loading…