Acetic Acid → HCID 9842523, compound
Reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C.O.[CH2:36]([OH:40])[CH2:37][CH2:38][CH3:39]>>[CH2:36]([O:40][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:8]=[C:7]([C:21]([F:24])([F:23])[F:22])[N:6]=1)[CH2:37][CH2:38][CH3:39]Participants
Conditions
- Temperature
- 50 °C
Procedure
A suspension of 2-(methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (525 g) in n-butanol (5.25 L) was treated with potassium carbonate (210 g) at 20±5° C. The mixture was heated to 50±5° C. overnight until the reaction was complete by HPLC. Acetic acid (1.57 L) was added dropwise, to control any gas evolution, keeping the temperature at 50±5° C. Water (3.67 L) was then added over 30 min keeping the temperature at 50±5° C. to allow full crystallisation to occur. The slurry was then cooled to 20-25° C. and aged for at least 1 hour. The resulting product was then filtered under vacuum and washed with a mixture of n-butanol (787 mL), acetic acid (236 mL), and water (551 mL) followed by water (2×1.57 L). The product was then dried at up to ca50° C. under vacuum to yield the title compound. Yield, 457 g, 88.4% of theory. The title compound was found to be identical to that of Example 10.
Workup
- customat 50±5° C
- customat 50±5° C.
- customcrystallisation
- temperatureThe slurry was then cooled to 20-25° C. and aged for at least 1 hour
- filtrationThe resulting product was then filtered under vacuum
- washwashed with a mixture of n-butanol (787 mL), acetic acid (236 mL), and water (551 mL)
- customThe product was then dried at up to ca50° C
Sources & evidence
- ORD record
- ord-59c6ebb0f25c46df858dba9416312438
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07026327B2
Reaction notes
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