Hydrochloric Acid → HCID 178418662, 화합물

HRID 37613

반응식

HRID 37613 반응식
[H-].[Na+].C(S)CC.[CH2:7]([C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[N:37](C4C=CC([N+]([O-])=O)=CC=4)[N:36]=[N:35][N:34]=3)=[CH:23][CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[CH3:8].[ClH:47]>CCCCCC.CN1CCCC1=O.O>[ClH:47].[CH2:7]([C:9]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:33]3[NH:37][N:36]=[N:35][N:34]=3)=[CH:25][CH:26]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[CH3:8]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 7848Propyl mercaptanHCID 24758Sodium hydrideHCID 199357842-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline

생성물 1

HCID 178418662HCID 178418662, 화합물수율 64%

시약·촉매·용매 3

HCID 962Water용매HCID 8058Hexane용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

Sodium hydride (50% dispersion in mineral oil; 0.091 g; 1.9 mmol) was washed with hexane, dried with a stream of nitrogen and covered with N-methylpyrrolidone (NMP) (5 ml). The mixture was cooled to below 10° C. and propanethiol (0.145 g; 1.9 mmol) was added slowly with stirring. After 15 minutes, a solution of 2-ethyl-4-[(2'-(1-(4-nitrophenyl)-1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline (A) (0.5 g; 0.95 mmol) in NMP (10 ml) was added slowly maintaining the temperature of the reaction mixture below 10° C. The mixture was then stirred for 2 hours. Concentrated hydrochloric acid was added until the reaction mixture was pH2. Water (25 ml) was then added and the suspended white solid collected by filtration. The crude product was recrystallised from ethanol to give 2-ethyl-4-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methoxy]quinoline hydrochloride as a solid, in 64% yield; m.p. 178°-181° C.; NMR (d6 -DMSO): 1.53(3H, t), 3.30(2H, q), 5.65(2H, s), 7.25(2H, d), 7.50-7.75(6H, m), 7.80(1H, t), 7.90(1H, s), 8.00(1H, t), 8.35(1H, d), 8.50(1H, d).

후처리

  1. customdried with a stream of nitrogen
  2. temperatureThe mixture was cooled to below 10° C.
  3. temperaturemaintaining the temperature of the reaction mixture below 10° C
  4. stirringThe mixture was then stirred for 2 hours
  5. filtrationthe suspended white solid collected by filtration
  6. customThe crude product was recrystallised from ethanol

출처 및 근거

ORD 기록
ord-e87f45f169df444b935b6b0d7d41c90c
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420292

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