p-Toluenesulfonic acid monohydrate → HCID 58503962, compound

HRID 2407701Notes

Reaction equation

HRID 2407701 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[O:37][N:36]=[C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:34]=3)[CH2:28][CH2:27]1)[C:18](O)([C:44]([O:46][CH3:47])=[O:45])[CH:17]2[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C1(C)C=CC=CC=1>[Br:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20](=[O:24])[N:19]([CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]3[O:37][N:36]=[C:35]([C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:34]=3)[CH2:28][CH2:27]1)[C:18]([C:44]([O:46][CH3:47])=[O:45])=[C:17]2[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58504183HCID 58504183, compound

Product 1

HCID 58503962HCID 58503962, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.070 g) was added to a suspension of the compound prepared in Example 95 (0.56 g) in toluene (20 mL). The reaction mixture was heated at reflux under Dean-Stark conditions overnight. The reaction mixture was then cooled to room temperature and partitioned between dichloromethane and a saturated aqueous sodium bicarbonate solution. The combined organics were dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:2) to obtain the title compound (0.35 g) having the following physical data.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under Dean-Stark conditions overnight
  3. custompartitioned between dichloromethane
  4. dry with materialThe combined organics were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=3:2)

Sources & evidence

ORD record
ord-29f793264c094ca681bc38eea89e84d3
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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