Triethylamine → HCID 87732437, compound

HRID 2377263Notes

Reaction equation

HRID 2377263 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7](O)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:32]=[C:33]3[C:47](=[CH:48][CH:49]=2)[C:36]2[NH:37][N:38]=[C:39]([C:40]4[S:44][C:43]([CH:45]=[O:46])=[CH:42][CH:41]=4)[C:35]=2[CH2:34]3)[CH2:26][CH2:25]1.C(N(CC)CC)C>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:37]2[C:36]3[C:47]4[C:33]([CH2:34][C:35]=3[C:39]([C:40]3[S:44][C:43]([CH:45]=[O:46])=[CH:42][CH:41]=3)=[N:38]2)=[CH:32][C:31]([CH2:30][N:27]2[CH2:28][CH2:29][N:24]([CH3:23])[CH2:25][CH2:26]2)=[CH:49][CH:48]=4)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 69768p,p'-Dimethoxybenzhydryl alcoholHCID 178480813HCID 178480813, compound

Product 1

HCID 87732437HCID 87732437, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To 4,4′-dimethoxybenzhydrol (5.62 g, 23.0 mmol) was carefully added thionyl chloride (20.1 mL, 276 mmol) and the mixture was heated to reflux for about 1 hour. The solution was cooled, evaporated to dryness and the residue was dissolved in tetrahydrofuran (50 mL). This solution was then added to a solution of Example 326 (5.3 g, 14.0 mmol) and triethylamine (5.9 mL, 42.0 mmol) in tetrahydrofuran (100 mL). The reaction mixture was heated to about 50° C. for about 2.5 hours, cooled, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum, and the residue was purified by flash chromatography on silica gel using dichloromethane/methanol (10:1) as eluent to provide the desired product. MS (ESI): m/z 605 (M+H)+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 1 hour
  3. temperatureThe solution was cooled
  4. customevaporated to dryness
  5. dissolutionthe residue was dissolved in tetrahydrofuran (50 mL)
  6. temperaturecooled
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f8132b92f19040cc90667a023b284bdf
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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