Hydrogen Bromide → 1-(5-Bromo-6-hydroxy-1,3-benzothiazol-2-yl)-3-ethyl-urea
Reaction equation
[Br:1][C:2]1[C:3]([O:17]C)=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1.Br.[OH-].[Na+]>>[Br:1][C:2]1[C:3]([OH:17])=[CH:4][C:5]2[S:9][C:8]([NH:10][C:11]([NH:13][CH2:14][CH3:15])=[O:12])=[N:7][C:6]=2[CH:16]=1Participants
4
Conditions
- Temperature
- 110 °C
Procedure
Intermediate 6 (1.30 g, 3.94 mmol) was suspended in hydrogen bromide solution (6.82 mL, 47% aq., 59.1 mmol) and the resulting suspension warmed to 110° C. Hydrogen bromide solution (14 mL, 47% aq., 121.3 mmol) was added portion-wise over the course of the reaction. After 47 h, the reaction mixture was cooled to RT then in ice and the pH adjusted with sodium hydroxide solution (1 M, aq.) to pH 8. The mixture was filtered and the resulting solid washed with H2O and ACN. The solid was sucked dry to give i (1.01 g, 81%). MS 315.87 & 317.84 [M+H]+.
Workup
- customover the course of the reaction
- temperaturethe reaction mixture was cooled to RT
- filtrationThe mixture was filtered
- washthe resulting solid washed with H2O and ACN
- customThe solid was sucked dry
- customto give i (1.01 g, 81%)
Sources & evidence
- ORD record
- ord-10620affaffa455f9b56b0d9b686d904
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08906902B2
Reaction notes
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