Dicyclohexylcarbodiimide → HCID 178480350、化合物

HRID 54892

反応式

HRID 54892 の反応式
[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH3:18])[CH:12]=[CH:13][C:14]=1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:20][C:21]1[S:22][CH2:23][CH2:24][N:25]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH3:18])[CH:12]=[CH:13][C:14]=1[C:15]([SH:22]1[CH2:23][CH2:24][NH:25][C:21]1=[S:20])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 117773263-benzyloxy-4-carboxy-1-methyl-2(1H)-pyridinoneHCID 178527880HCID 178527880、化合物

生成物 1

HCID 178480350HCID 178480350、化合物収率 80.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-benzyloxy-4-carboxy-1-methyl-2(1H)-pyridinone (1.05 g, 4 mmol), 2-mercaptothiazoline (0.50 g, 4.2 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) in dry methylene chloride (50 mL), N,N'-dicyclohexylcarbodiimide (DCC) (0.86 g, 4.2 mmol) is added. Alter stirring for 4 hours, the dicyclohexylurea (DCU) solids are removed by filtration, the yellow filtrate is rotary evaporated to give a yellow solid. Crystallization from isopropanol-methylene chloride gives the title compound (1.16 g, 80.4%) as bright yellow crystalline plates, m.p. 149°-150° C. 1H NMR (250 MHz, CDCl3) δ2.867 (t, 2H, J=7.32), 3.594 (s, 3H), 4.313 (t, 2H, J=7.33), 5.301 (s, 2H), 6.107 (d, 1H, J=6.99), 7.126 (d, 1H, J=7.00), 7.31-7.45 (m, 5H). Anal for C17H16N2O3S2Calcd. (found): C, 56.64 (56.36); H, 4.47 (4.47); N, 7.73 (7.73); S, 17.78 (17.41).

後処理

  1. customthe dicyclohexylurea (DCU) solids are removed by filtration
  2. customthe yellow filtrate is rotary evaporated
  3. customto give a yellow solid
  4. customCrystallization from isopropanol-methylene chloride

出典と根拠

ORDレコード
ord-2eccfe09b9cb46afbcd6f13ab1c25065
出典データセット
uspto-grants-1997_04
特許番号
US05624901

関連ノート

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