Diisopropylethylamine → 2-Chlorobenzene-1-sulfonic acid

HRID 482092ノート

反応式

HRID 482092 の反応式
N1CCCC(COC2C=C([O:16][S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])(=[O:19])=[O:18])C=C(C)C=2)C1.C(N(CC)C(C)C)(C)C.NN=CS(O)(=O)=O>CN(C=O)C>[Cl:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([OH:19])(=[O:18])=[O:16]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 3013981Aminoiminomethane-sulphonic acidHCID 536550322-Chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester

生成物 1

HCID 135314532-Chlorobenzene-1-sulfonic acid収率 82.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2-chlorobenzenesulfonic acid 3-[(piperidin-3-yl)methoxy]-5-methylphenyl ester (396 mg, 1.0 mmol), as prepared in the preceding step, in DMF (10 mL) containing N,N-diisopropylethylamine (0.5 mL) and aminoiminomethanesulfonic acid (248 mg, 2.0 mmol) was stirred at room temperature overnight. The DMF was removed in vacuo and the residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3) to give the title compound as a white foam (159 mg, 36%). 1H-NMR (300 MHz, CDCl3) δ 1.45-1.92 (m, 4H), 2.11 (m, 1H), 2.23 (s, 3H), 3.07 (m, 2H), 3.81 (d, 2H), 3.92 (m, 2H), 6.50 (s, 2H), 6.61 (s, 1H), 7.24 (bs, 3H), 7.40 (m, 1H), 7.63 (m, 2H), 7.95 (dd, 1H). Mass spectrum (MALDI-TOF, sinapinic acid matrix) calcd. for C20H24N3 O4SCl: 438.1 (M+H), 460.1 (M+Na), Found: 438.5, 460.5.

後処理

  1. customThe DMF was removed in vacuo
  2. customthe residue was purified by flash column chromatography (90:10 methylene chloride:methanol saturated with NH3)

出典と根拠

ORDレコード
ord-c3554de2a0044adfa27dfbcc7fab88a2
出典データセット
uspto-grants-1998_08
特許番号
US05792769

反応ノート

読み込み中…