2,3-Dichloropropene → HCID 21875394、化合物

HRID 1441806ノート

反応式

HRID 1441806 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[SH:11].[Cl:12][C:13]([CH2:15]Cl)=[CH2:14].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11][CH2:15][C:13]([Cl:12])=[CH2:14]

参加物

7

反応物 4

HCID 65652,3-DichloropropeneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 47130122-chloro-5-nitrobenzenethiol

生成物 1

HCID 21875394HCID 21875394、化合物収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-chloro-5-nitro-benzenethiol (1.0 g, 5.27 mmol, prepared in accordance with the procedure described by Still et al. Synth. Comm. 13, 1181 (1983)) in 15 mL DMF was treated with 2,3-dichloropropene (693 μL, 7.52 mmol) and K2CO3 (433 mg, 3.13 mmol). The mixture was heated at 80° C. for 2 h and then allowed to cool to rt. EtOAc (200 mL) and H2O (100 mL) were added. The organic phase was washed with H2O (2×250 mL), saturated aqueous NaCl (100 mL), dried over MgSO4, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes to give compound 260A (1.09 g, 89%) as an orange oil.

後処理

  1. temperatureto cool to rt
  2. washThe organic phase was washed with H2O (2×250 mL), saturated aqueous NaCl (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash column chromatography on silica gel eluting with 20% EtOAc in hexanes

出典と根拠

ORDレコード
ord-85ca8677847f47aeb437bb00412db972
出典データセット
uspto-grants-2010_02
特許番号
US07655689B2

反応ノート

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