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Phosphorus oxychloride → 4-Chloro-6-(difluoromethoxy)-2-[[(2,3-difluorophenyl)methyl]thio]-pyrimidine

HRID 1024855
ノート
印刷プレビュー

反応式

HRID 1024855 の反応式
[F:1][CH:2]([F:21])[O:3][C:4]1[N:9]=[C:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[N:7]=[C:6](O)[CH:5]=1.P(Cl)(Cl)([Cl:24])=O>COCCOC.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:24][C:6]1[CH:5]=[C:4]([O:3][CH:2]([F:21])[F:1])[N:9]=[C:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=2[F:19])[N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 24813Phosphorus oxychlorideHCID 1785166036-(Difluoromethoxy)-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinol2 回

生成物 1

HCID 866198714-Chloro-6-(difluoromethoxy)-2-[[(2,3-difluorophenyl)methyl]thio]-pyrimidine

試薬・触媒・溶媒 3

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒
HCID 8071
1,2-Dimethoxyethane
溶媒

実験手順

To a solution of 6-(difluoromethoxy)-2-[[(2,3-difluorophenyl)methyl]thio]-4-pyrimidinol (product of step i) (0.4 g) in 1,2-dimethoxyethane was added benzyltriethylammonium chloride (3 mg) and phosphorous oxychloride (0.23 mL). The resulting mixture was heated to reflux for 16 hours. The reaction mixture was cooled then diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O and dried (MgSO4), filtered and evaporated. Purification was by column chromatography on silica gel using EtOAc/isohexane (2:8) as eluent to give the subtitle compound as a clear, colourless oil. Yield: 0.35 g

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with H2O
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customPurification

出典と根拠

ORDレコード
ord-d654dbca5a7b4176b7ef4dbbd631c163
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08722883B2

反応ノート

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