Methyl iodide → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime

HRID 989224ノート

反応式

HRID 989224 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH:19]=[N:20][OH:21])[C:3]=1[S:22]([CH3:24])=[O:23].[O-][CH2:26]C.[Na+].IC>C(O)C>[CH3:26][O:21][N:20]=[CH:19][C:4]1[C:3]([S:22]([CH3:24])=[O:23])=[C:2]([NH2:1])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=1

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 2723922Sodium ethoxideHCID 1363524165-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime

生成物 1

HCID 545293625-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime収率 39.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

A solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde oxime (0.15 g) in ethanol was added to a solution of sodium ethoxide (0.025 g) in ethanol at 20° C., followed by iodomethane (0.023 ml). The reaction was monitored by HPLC and over the next 24 hours three additional equivalents of iodomethane were added. The reaction mixture was then, concentrated and partitioned between dichloromethane and water. The organic layer was water-washed, dried (MgSO4) and concentrated. This was then combined with crude product from another identical preparation and chromatographed on a silica gel column, eluting with hexane/ethyl acetate, to give 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinyl-1H-pyrazole-3-carboxaldehyde O-(methyl)oxime (0.06 g) as a yellow solid m.p.80° C. Compound 17.

後処理

  1. additionwere added
  2. concentrationconcentrated
  3. custompartitioned between dichloromethane and water
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThis was then combined with crude product from another identical preparation
  8. customchromatographed on a silica gel column
  9. washeluting with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-e404aca62405486785ab5eaec48067c8
出典データセット
uspto-grants-2003_10
特許番号
US06638956B2

反応ノート

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