Dichloromethane → Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

HRID 1585952ノート

反応式

HRID 1585952 の反応式
[OH:1][CH2:2][CH2:3][CH:4]([C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.C(Cl)Cl.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(C(C)C)CC)(C)C>C1COCC1>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH:4]([N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH2:3][CH2:2][O:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:11][CH:12]=1)#[N:15]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 187796904-(3-Hydroxy-1-imidazol-1-yl-propyl)-benzonitrile

生成物 1

HCID 54062353Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The 4-(3-hydroxy-1-imidazol-1-yl-propyl)-benzonitrile (1.4 gm, 6.16 mmol) was suspended in 2:1 methylene chloride: THF (100 mL) under argon and cooled to 0° C. in an ice bath. Methanesulfonylchloride (1 mL, 12.4 mmol) was added followed by diisopropylethylamine (3.22 mL, 18.5 mmol). The reaction was stirred for 4 hours and the solvent was removed in vacuo. The residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel using using 1:3 ethyl acatate: hexanes. The desired fractions were concentrated in vacuo to give the desired product.

後処理

  1. customthe solvent was removed in vacuo
  2. extractionextracted 2 times with saturated aqueous sodium bicarbonate (100 mL)
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel using
  5. concentrationThe desired fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-7ec47d98df8649f48916f77bebdebe42
出典データセット
uspto-grants-1999_08
特許番号
US05939439

反応ノート

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