Ethyl Acetate → 150726-52-6
Reaction equation
C[O-].[Na+:3].[CH3:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[N:23]=[C:22]([C:24]3[N:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[N:21]=[C:20]([O:30][CH2:31][CH2:32][OH:33])[C:19]=2[O:34][C:35]2[C:40]([O:41][CH3:42])=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)([CH3:7])[CH3:6].O.C(OCC)(=O)C>CO>[CH3:7][C:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N-:17][C:18]2[C:19]([O:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:40]=3[O:41][CH3:42])=[C:20]([O:30][CH2:31][CH2:32][OH:33])[N:21]=[C:22]([C:24]3[N:25]=[CH:26][CH:27]=[CH:28][N:29]=3)[N:23]=2)(=[O:15])=[O:16])=[CH:10][CH:9]=1)([CH3:4])[CH3:6].[Na+:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
Sodium methoxide solution (30% methanolic solution; 3.9 mL) was added to a mixture of bosentan monohydrate (5 g) in methanol (15 mL). Ethyl acetate (80 mL) was added to the reaction mixture. The reaction mixture was heated to 55° C. and stirred for 30 minutes at 55° C. The reaction mixture was cooled to 25° C. The reaction mixture was stirred for 1.5 hours and the solid was filtered at 10° C. to 15° C., washed with a mixture of ethyl acetate (4 mL) and methanol (1 mL). The wet material obtained was dried at hot air oven at 50° C. to 55° C. to obtain the title compound.
Workup
- temperatureThe reaction mixture was cooled to 25° C
- stirringThe reaction mixture was stirred for 1.5 hours
- filtrationthe solid was filtered at 10° C. to 15° C.
- washwashed with a mixture of ethyl acetate (4 mL) and methanol (1 mL)
- customThe wet material obtained
- customwas dried at hot air oven at 50° C. to 55° C.
Sources & evidence
- ORD record
- ord-03ed4d6965414196a81b0182ba5005f6
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08716477B2
Reaction notes
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