Triethylamine → 2-(2,6-difluorophenyl)-4-(4-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine

HRID 962434ノート

反応式

HRID 962434 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:12])[CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=1[C:23](Cl)=O>O1CCCC1>[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:22]=1[C:23]1[O:11][CH2:10][CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 874382,6-Difluorobenzoyl chlorideHCID 170394353-Amino-3-(4-chlorophenyl)propan-1-ol

生成物 1

HCID 157907332-(2,6-difluorophenyl)-4-(4-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine収率 35.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 0.9 g of 3-(4-chlorophenyl)-3-amino-1-propanol, 0.5 g of triethylamine in 10 ml of tetrahydrofuran at 0° C., was added dropwise 0.8 g of 2,6-difluorobenzoyl chloride. The reaction mixture was stirred at room temperature for 5 hours. The precipitated solid was filtered off and the filtrate was concentrated under reduced pressure. To the residue, there was added 20 ml of tetrahydrofuran and 2.4 g of triphenylphosphine and further added 2.0 g of diisopropyl azodicarboxylate. The reaction mixture was stirred at room temperature for 12 hours and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to afford 0.5 g of 2-(2,6-difluorophenyl)-4-(4-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine. ND23.2 1.5532

後処理

  1. filtrationThe precipitated solid was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue, there was added 20 ml of tetrahydrofuran and 2.4 g of triphenylphosphine and further added 2.0 g of diisopropyl azodicarboxylate
  4. stirringThe reaction mixture was stirred at room temperature for 12 hours
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-799a71b1a8f84c518618ef4d68cd812e
出典データセット
uspto-grants-1998_06
特許番号
US05760033

反応ノート

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