2-Bromo-6-phenylcyclohexanone → (3-Methoxy-4-oxazol-5-yl-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2075974

反応式

HRID 2075974 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15]([NH2:17])=[S:16])[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1.Br[CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20]1=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15]2[S:16][C:27]3[CH2:28][CH2:29][CH2:30][CH:25]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:19][CH:20]=4)[C:26]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1

参加物

4

反応物 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 22459682(3-Methoxy-4-oxazol-5-yl-phenyl)-thiourea

生成物 1

HCID 57780726(3-Methoxy-4-oxazol-5-yl-phenyl)-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine収率 83.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of (3-methoxy-4-oxazol-5-yl-phenyl)-thiourea (74.8 mg, 0.3 mmol) and of 2-bromo-6-phenyl-cyclohexanone (75.9 mg, 0.3 mmol, preparation: WO9404487) in ethanol (4 mL) was heated over night to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was purified on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (101 mg, 83%) as an off-white foam. MS ISP (m/e): 404.5 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.29 (s, 1H), 8.31 (s, 1H), 7.66 (s, 1H), 7.50 (d, 1H), 7.46-7.51 (m, 3H), 7.09-7.31 (m, 3H), 6.83 (s, 1H), 4.00 (m, 1H), 3.46 (s, 3H), 2.73 (m, 2H), 2.12 (m, 1H), 1.70-1.94 (m, 3H).

後処理

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customwas evaporated under reduced pressure
  3. customthe residue was purified on silica gel

出典と根拠

ORDレコード
ord-f7d6574307724d029c3157fc7e6614fe
出典データセット
uspto-grants-2011_04
特許番号
US07923450B2

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