Triethylamine → Ammonium hydroxide methanol

HRID 379032ノート

反応式

HRID 379032 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C([N:13](CC)CC)C.CS(Cl)(=O)=O.[OH:23][C:24]1[CH:31]=[C:30]([CH2:32][N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].[C:38](=O)([O-])[O-:39].[Cs+].[Cs+]>C(Cl)Cl.CN(C=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([O:23][C:24]2[CH:31]=[C:30]([CH2:32][N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)[CH:29]=[CH:28][C:25]=2[C:26]#[N:27])[CH3:7])=[CH:9][CH:10]=1.[CH3:38][OH:39].[NH4+:13].[OH-:8]

参加物

9

反応物 5

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 74647p-Chlorophenethylic alcoholHCID 216970282-Hydroxy-4-imidazol-1-ylmethyl-benzonitrile

生成物 2

HCID 21697126HCID 21697126、化合物HCID 21894508Ammonium hydroxide methanol収率 0.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

4-chlorophenethyl alcohol (0.11 g, 0.67 mmol) and triethylamine (0.37 mL, 2.68 mmol) were dissolved in CH2Cl2 (5 mL) at 0° C. Then it was treated with methanesulfonyl chloride (0.207 mL, 2.68 mmol), with stirring and warming to ambient temperature, until the indicated loss of starting material. The reaction mixture was concentrated in vacuo, then dissolved in DMF (1 mL) and added to a mixture of 2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile (0.10 g, 0.50 mmol) and cesium carbonate (0.33 g, 1.0 mmol) in DMF (2 mL). The reaction mixture was heated at 30° C. for 18 h, then partitioned between EtOAc and H2O, the aqueous layer washed with EtOAc, the organic layers combined, washed with brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound after silica gel chromatography (0.1 to 0.2% CH3OH/NH4OH in CH2Cl2) and conversion to the hydrochloride salt.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in DMF (1 mL)
  3. temperatureThe reaction mixture was heated at 30° C. for 18 h
  4. custompartitioned between EtOAc and H2O
  5. washthe aqueous layer washed with EtOAc
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and concentration to dryness

出典と根拠

ORDレコード
ord-256d2ec089464070aa37ed5f7c8c0bca
出典データセット
uspto-grants-2001_10
特許番号
US06297239B1

反応ノート

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