150726-52-6 → Bosentan hydrate

HRID 1427341Notes

Reaction equation

[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N-:14][C:15]2[N:20]=[C:19]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=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:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[Na+]>CC(C)=O>[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:26]=[CH:25][CH:24]=[CH:23][N:22]=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].[OH2:12]

Participants

Conditions

Temperature: 55 °C

Procedure

40 g of Bosentan sodium salt were dissolved in acetone (353 g) and 8.48 g of hydrochloridric acid were added. Precipitated salts were filtered off and the clear solution was concentrated by distillation to a residual volume of 190 mL. The mixture was cooled to 55° C. and demineralized water (58 g) was slowly dropped keeping the temperature at 55° C. After 2 hours aging the temperature was decreased to 20° C. in 1 hour and stirred for additional 2 hours at that temperature. The precipitated solid was collected by filtration and the cake was washed with water-acetone 1:1 (38 g). 39.4 g of the desired product were obtained after drying in vacuo.

Workup

filtrationPrecipitated salts were filtered off
concentrationthe clear solution was concentrated by distillation to a residual volume of 190 mL
additiondemineralized water (58 g) was slowly dropped
customat 55° C
waitthe temperature was decreased to 20° C. in 1 hour
filtrationThe precipitated solid was collected by filtration
washthe cake was washed with water-acetone 1:1 (38 g)

Sources & evidence

ORD record: ord-a245c20cfe564491ac6472e2d1b6df74
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933226B2

Reaction notes

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