Dichloromethane → (2-Cyano-4-methoxycarbonyl-phenyl)-trimethyl-ammonium trifluoro-methanesulfonate

HRID 1041845ノート

反応式

HRID 1041845 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:12])[CH3:11])=[C:6]([C:13]#[N:14])[CH:5]=1.Cl[CH2:17]Cl.C[O:20][S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22]>C(OCC)C>[F:25][C:24]([F:27])([F:26])[S:21]([O-:23])(=[O:22])=[O:20].[C:13]([C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:9]=[CH:8][C:7]=1[N+:10]([CH3:17])([CH3:11])[CH3:12])#[N:14]

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 9526Methyl triflateHCID 598476573-Cyano-4-dimethylamino-benzoic acid methyl ester

生成物 1

HCID 86621519(2-Cyano-4-methoxycarbonyl-phenyl)-trimethyl-ammonium trifluoro-methanesulfonate収率 69%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a stirred solution of 6.16 g (30.2 mmol) 3 and 110 ml dichloromethane were added 50.0 g (302 mmol) methyltriflate (Aldrich) drop wisely. The reaction mixture was stirred over night and diethylether was added. After evaporation of one third of the solvent volume the desired compound precipitates and the rest of the solvent were decanted. The solid was washed extensively (ten times) with large amounts of diethylether. The solid was dried by use of oil pump vacuum and purified by (C-18) RP-column chromatography (acetonitril/water—gradient 1:99 to 80:20). The desired compound 4 was obtained in 69% yield (20.8 mmol, 7.68 g).

後処理

  1. customAfter evaporation of one third of the solvent volume the desired compound
  2. customprecipitates
  3. customthe rest of the solvent were decanted
  4. washThe solid was washed extensively (ten times) with large amounts of diethylether
  5. customThe solid was dried by use of oil pump vacuum
  6. custompurified by (C-18) RP-column chromatography (acetonitril/water—gradient 1:99 to 80:20)

出典と根拠

ORDレコード
ord-14848f56a14a460f8cd5383286b8ca90
出典データセット
uspto-grants-2013_10
特許番号
US08557776B2

反応ノート

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