Dabco → Azoxystrobin

HRID 1645232

反応式

HRID 1645232 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].C1N2[CH2:35][CH2:36][N:31](CC2)C1>CN(C=O)C>[C:36]([C:35]1[CH:11]=[CH:10][CH:9]=[CH:14][C:23]=1[O:26][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2/[C:15](=[CH:20]\[O:21][CH3:22])/[C:16]([O:18][CH3:19])=[O:17])[CH:3]=1)#[N:31]

参加物

5

反応物 3

HCID 9237DabcoHCID 11430Potassium CarbonateHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

生成物 1

HCID 3034285Azoxystrobin収率 83.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of methyl (E)-2-{2-[6-chloropyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (96.2 g; prepared as described in WO 92/08703) in DMF (approximately 100 g) was added a DMF solution of 2-cyanophenyl (78.5 g at 50% w/w 2-cyanophenyl) followed by potassium carbonate (63.5 g) and DABCO (0.34 g). The mixture was heated to 80° C. and held for 75 minutes. The DMF was removed by vacuum distillation to a final temperature of 100° C. Toluene (165.8 g) was charged to the distillation residues and the temperature brought to 75° C. before adding hot water (318.6 g) and stirring for 30 minutes at 80° C. The aqueous phase was removed and then the toluene layer was sampled and analysed. The solution yield of methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (azoxystrobin) was 90.0%. The toluene was distilled off under vacuum. Methanol (88 g) was added to the distillation residues at 70° C. and the mixture cooled to <5° C., filtered and the cake washed with methanol (2×30 ml) to give, after drying, methyl (E)-2-{2-[6-(2-cyano-phenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (83.2% yield).

後処理

  1. customThe DMF was removed by vacuum distillation to a final temperature of 100° C
  2. additionToluene (165.8 g) was charged to the distillation residues
  3. custombrought to 75° C.
  4. additionbefore adding hot water (318.6 g)
  5. customThe aqueous phase was removed
  6. aliquotthe toluene layer was sampled
  7. distillationThe toluene was distilled off under vacuum
  8. additionMethanol (88 g) was added to the distillation residues at 70° C.
  9. temperaturethe mixture cooled to <5° C.
  10. filtrationfiltered
  11. washthe cake washed with methanol (2×30 ml)
  12. customto give
  13. customafter drying

出典と根拠

ORDレコード
ord-06c8aa0c775c47019512e4f701262840
出典データセット
uspto-grants-2012_02
特許番号
US08124761B2

関連ノート

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