Methanesulfonic Acid → HCID 131723755, 화합물

HRID 1057649노트

반응식

HRID 1057649 반응식
[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

참가 물질

5

반응물 2

HCID 6395Methanesulfonic AcidHCID 9841354HCID 9841354, 화합물

생성물 1

HCID 131723755HCID 131723755, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-75e7519a69dc46ef891baec3715ed40f
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514968B1

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