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Dimethylformamide → 5-bromo-4-chloro-2-(3-cyano-propoxy)-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 448933
ノート
印刷プレビュー

反応式

HRID 448933 の反応式
CN(C=O)C.[Br:6][C:7]1[C:8]([Cl:26])=[CH:9][C:10]([OH:25])=[C:11]([CH:24]=1)[C:12]([N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH3:15])=[O:13].Br[CH2:28][CH2:29][CH2:30][C:31]#[N:32].C([O-])([O-])=O.[K+].[K+]>ClCCl>[Br:6][C:7]1[C:8]([Cl:26])=[CH:9][C:10]([O:25][CH2:28][CH2:29][CH2:30][C:31]#[N:32])=[C:11]([CH:24]=1)[C:12]([N:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[CH3:15])=[O:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2 回HCID 214124-Bromobutyronitrile2 回HCID 686025845-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide

生成物 1

HCID 686035255-bromo-4-chloro-2-(3-cyano-propoxy)-N-(2-methoxy-phenyl)-N-methyl-benzamide収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

To a stirring DMF solution (6 mL) containing 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (300 mg, 0.81 mmol) was added 4-bromo-butyronitrile (0.096 mL, 0.97 mmol) and K2CO3 (223 mg, 1.62 mmol). The mixture was heated at 50° C. for 8 hrs. Additional 0.5 eq. of 4-bromobutyronitrile and 0.5 eq of K2CO3 were added and the mixture was heated for another 8 hrs. The mixture was diluted with dichloromethane, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified via silica gel flash column chromatography to afford 5-bromo-4-chloro-2-(3-cyano-propoxy)-N-(2-methoxy-phenyl)-N-methyl-benzamide (241 mg). MS [M+H]+: 439.1; tR=2.62 min (method 1)

後処理

  1. temperaturethe mixture was heated for another 8 hrs
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via silica gel flash column chromatography

出典と根拠

ORDレコード
ord-73927f8442034b60904cb71e2fcf76ff
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481738B2

反応ノート

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