Potassium Carbonate → Azoxystrobin
Reaction equation
[K].[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])#[N:3].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]([CH:36](OC)[O:37][CH3:38])[C:32]([O:34][CH3:35])=[O:33])[CH:19]=1>O>[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:18]1[N:23]=[CH:22][N:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2/[C:31](=[CH:36]\[O:37][CH3:38])/[C:32]([O:34][CH3:35])=[O:33])[CH:19]=1)#[N:3]Participants
Conditions
- Temperature
- 70 °C
Procedure
Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate in methylcyclohexane/chloromethoxypyrimidine (185.5 g, 59.71% strength) was vacuum distilled to leave the propanoate melt. A solution of the potassium salt of 2-cyanophenol was then prepared by mixing 2-cyanophenol (49.0 g) and potassium carbonate (30.4 g) in water (50 g). This solution was added to the methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate melt, which had previously been cooled to 70° C. The reaction solution was then heated to 120° C. and held for 2 hours. Any distillates were allowed to come off under atmospheric conditions. (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate was produced (39.4 area %). The reaction solution was then distilled under vacuum (20 mmHg) at 95° C. for 2 hours and at 120° C. for 1 hour. No further demethanolysis was evident. The reagents were cooled to 95° C. before an additional amount of potassium carbonate (45.6 g) was charged. The solution was again distilled under vacuum (20 mmHg) at 95° C. for 20 minutes and at 120° C. for 20 mins. (E)-Methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate was produced (55.6 area %).
Workup
- temperatureThe reaction solution was then heated to 120° C.
Sources & evidence
- ORD record
- ord-586cafcc517f48fca0e9a0299f2d93ca
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06153750
Reaction notes
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