Methanesulfonic Acid → HCID 131723755、化合物

HRID 1057649ノート

反応式

HRID 1057649 の反応式
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([O:22][CH2:23][CH2:24][NH2:25])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][S:27]([OH:30])(=[O:29])=[O:28]>CO.ClCCl>[CH3:26][S:27]([OH:30])(=[O:29])=[O:28].[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([Cl:21])=[C:16]([O:22][CH2:23][CH2:24][NH2:25])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 6395Methanesulfonic AcidHCID 9841354HCID 9841354、化合物

生成物 1

HCID 131723755HCID 131723755、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To [(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]acetonitrile (0.292 g, 0.842 mmol) in THF (6 mL) is added borane-methyl sulfide complex (0.24 mL, 2.53 mmol). The mixture is stirred at 80° C. for 2.5 h and then allowed to cool. MeOH is carefully added to the residue until gas evolution ceased and then the mixture is concentrated under vacuum. MeOH addition/removal is repeated two more times and then MeOH-dichloromethane (about 2 mL each) is added, followed by several drops of conc. HCl. The mixture is stirred for about 15 min and then taken to dryness under vacuum. After partitioning with dichloromethane and aq. sodium bicarbonate and drying, the residue is chromatographed on silica gel (50 mL) using MeOH-dichloromethane (2/98 to 4/96) to give 0.206 g (70%) of 2-[(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]ethylamine. The methanesulfonate salt is prepared by dissolving 2-[(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]ethylamine in MeOH and dichloromethane and adding methanesulfonic acid (0.0581 g). The mixture is concentrated to dryness under vacuum and the residue is crystallized from dichloromethane-hexane to give 0.206 g of 2-[(9-benzyl-3-chloro-9H-carbazol-4-yl)oxy]ethylamine, methanesulfonate salt as a white crystalline solid. 1H NMR (CDCl3) δ1.9, 3.29, 4.31, 5.49, 7.07, 7.12, 7.27, 7.35-7.49, 8.32.

後処理

  1. concentrationThe mixture is concentrated to dryness under vacuum
  2. customthe residue is crystallized from dichloromethane-hexane

出典と根拠

ORDレコード
ord-75e7519a69dc46ef891baec3715ed40f
出典データセット
uspto-grants-2003_02
特許番号
US06514968B1

反応ノート

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