2-Bromo-6-phenylcyclohexanone → (4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-pyridin-4-yl-phenyl)-amine

HRID 2076135ノート

反応式

HRID 2076135 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]1=O>C(O)C>[C:20]1([CH:24]2[C:25]3[N:16]=[C:14]([NH:13][C:10]4[CH:9]=[CH:8][C:7]([C:4]5[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=5)=[CH:12][CH:11]=4)[S:15][C:26]=3[CH2:27][CH2:28][CH2:29]2)[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=1

参加物

4

反応物 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632614(4-Pyridin-4-yl-phenyl)-thiourea

生成物 1

HCID 44194155(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-pyridin-4-yl-phenyl)-amine収率 20.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of (4-pyridin-4-yl-phenyl)-thiourea (100 mg, 0.44 mmol) and 2-bromo-6-phenyl-cyclohexanone (116 mg, 0.46 mmol) in ethanol (5 ml) was heated to reflux over night. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel using methylene chloride and methylene chloride/methanol (19:1 v/v) as the eluent to yield the title compound (34 mg, 20%) as a yellow solid. MS ISP (m/e): 384.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=8.61 (d, 2H), 7.59 (d, 2H), 7.46 (d, 1H), 7.18-7.33 (m, 5H), 7.13 (d, 2H), 4.08 (m, 1H), 2.75 (m, 2H), 2.18 (m, 1H), 1.7-1.98 (m, 3H).

後処理

  1. temperatureto reflux over night
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-b5c3ab6531d04e63bf00583ca60bc0de
出典データセット
uspto-grants-2011_04
特許番号
US07923450B2

反応ノート

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