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Thionyl Chloride → HCID 22174481、化合物

HRID 1797308
ノート
印刷プレビュー

反応式

HRID 1797308 の反応式
[CH2:1]([O:3][P:4]([CH2:9][C:10]([OH:12])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:23]=[C:22]([Br:24])[CH:21]=[CH:20][C:19]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[CH3:40])=[O:33])=[C:28]([Cl:41])[CH:27]=1.C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1.C(Cl)Cl>[Br:24][C:22]1[CH:21]=[CH:20][C:19]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[O:33])=[C:28]([Cl:41])[CH:27]=2)=[C:18]([NH:17][C:10](=[O:12])[CH2:9][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])[CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24386Thionyl ChlorideHCID 36704(Diethoxyphosphinyl)acetic acidHCID 81531DiisopropylethylamineHCID 9801969EO-1428

生成物 1

HCID 22174481HCID 22174481、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒
HCID 6344
Dichloromethane
溶媒
3 回

実験手順

The reactions were conducted under an argon atmosphere using oven dried glass ware. Diethylphosphonoacetic acid (0.085 mL, 0.53 mmol) was dissolved in dry toluene (1 mL) and thionylchloride (0.044 mL, 0.61 mmol) was added. The reaction mixture was refluxed for 1 h and then concentrated in vacuo. {4-[(2-Amino-4-bromophenyl)amino]-2-chlorophenyl}(2-methylphenyl)methanone (0.28 g, 0.48 mmol)(disclosed in WO 01/05744) was dissolved in dry DCM (1 mL) and N,N-diisopropylethyl amine (0.16 mL, 0.96 mmol) was added followed by drop wise addition of the above acid chloride dissolved in dry DCM (2.5 mL). The reaction mixture was stirred at room temperature for 22 h after which it was diluted with DCM. The organic phase was washed with 10% aqueous NaHCO3, H2O and brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc/petroleum ether 3:1 as the eluent to afford the title compound as an oil.

後処理

  1. customdried glass ware
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. concentrationconcentrated in vacuo
  4. washThe organic phase was washed with 10% aqueous NaHCO3, H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-8b23612ff3cb4a68bdab5a7b69b9d5be
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07034015B2

反応ノート

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