Hydrochloric Acid → HCID 178418662、化合物

HRID 5679

反応式

HRID 5679 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 178418662HCID 178418662、化合物収率 64%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8058Hexane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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 (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).

後処理

  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

出典と根拠

ORDレコード
ord-a42eab0e9842413eba4f462da9863058
出典データセット
uspto-grants-1993_09
特許番号
US05245035

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