Methane → Bosentan hydrate

HRID 2280509Notes

Reaction equation

HRID 2280509 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:16]([O:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=3[O:38][CH3:39])=[C:17]([O:27][CH2:28][CH2:29][OH:30])[N:18]=[C:19]([C:21]3[N:22]=[CH:23][CH:24]=[CH:25][N:26]=3)[N:20]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])[CH3:3].C.[OH2:41]>C(O)C>[CH3:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:20]=[C:19]([C:21]3[N:22]=[CH:23][CH:24]=[CH:25][N:26]=3)[N:18]=[C:17]([O:27][CH2:28][CH2:29][OH:30])[C:16]=2[O:31][C:32]2[C:37]([O:38][CH3:39])=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:1])[CH3:3].[OH2:41]

Participants

5

Reactant 3

HCID 297MethaneHCID 962WaterHCID 104865Bosentan

Product 1

HCID 185462Bosentan hydrateYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The wet Bosentan was dissolved in ethanol (4.4 lit) at 50° C. to 55° C. and decolorized with activated charcoal. The solution was heated at 50° C. to 55° C. To this solution, water (4.4 lit) was added and was stirred for 20 min. The solution was cooled to 25° C. to 30° C. and was maintained at same temperature for 60 min. The crystalline solid obtained was filtered, washed with chilled ethanol, and dried under vacuum (650-700 mm/Hg) at 35° C. to 40° C. to afford 2.20 kg [68.7% yield] of Bosentan monohydrate as a white crystalline solid.

Workup

  1. temperatureThe solution was heated at 50° C. to 55° C
  2. temperatureThe solution was cooled to 25° C. to 30° C.
  3. temperaturewas maintained at same temperature for 60 min
  4. customThe crystalline solid obtained
  5. filtrationwas filtered
  6. washwashed with chilled ethanol
  7. customdried under vacuum (650-700 mm/Hg) at 35° C. to 40° C.

Sources & evidence

ORD record
ord-7aa6cdf0f4d645408725ccdaab83db3b
Source dataset
uspto-grants-2015_09
Patent number
US09139537B2

Reaction notes

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