4-(1,2,4-Triazol-1-yl)phenylthiourea → (4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-[1,2,4]triazol-1-yl-phenyl)-amine

HRID 2075975

反応式

HRID 2075975 の反応式
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]([NH2:15])=[S:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.Br[CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=O>C(O)C>[C:19]1([CH:23]2[C:24]3[N:15]=[C:13]([NH:12][C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[N:4][CH:3]=[N:2]5)=[CH:11][CH:10]=4)[S:14][C:25]=3[CH2:26][CH2:27][CH2:28]2)[CH:20]=[CH:21][CH:22]=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 52606784-(1,2,4-Triazol-1-yl)phenylthioureaHCID 127791292-Bromo-6-phenylcyclohexanone

生成物 1

HCID 57399119(4-Phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-(4-[1,2,4]triazol-1-yl-phenyl)-amine収率 64.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A suspension of 4-(1,2,4-triazol-1-yl)phenylthiourea (109.6 mg, 0.5 mmol) and of 2-bromo-6-phenyl-cyclohexanone (253.1 mg, 1.00 mmol) in ethanol (4 mL) was heated for two days to reflux under an atmosphere of nitrogen. After cooling to room temperature the solvent was evaporated under reduced pressure and the residue was treated with dichloromethane, diethyl ether and heptane. The product precipitated as a solid and was filtered off to yield the title compound (120 mg, 64%) as a pale-brown solid. MS ISP (m/e): 374.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.4 (s, 1H), 9.38 (s, 1H), 8.29 (s, 1H), 8.02 (d, 2H), 7.56 (d, 2H), 7.30 (t, 2H), 7.10-7.19 (m, 5H), 4.00 (m, 1H), 2.72 (m, 2H), 2.14 (m, 1.70-1.89 (m, 3H).

後処理

  1. temperatureto reflux under an atmosphere of nitrogen
  2. customwas evaporated under reduced pressure
  3. additionthe residue was treated with dichloromethane, diethyl ether and heptane
  4. customThe product precipitated as a solid
  5. filtrationwas filtered off

出典と根拠

ORDレコード
ord-b010277627c24eb3b246654ff4874675
出典データセット
uspto-grants-2011_04
特許番号
US07923450B2

関連ノート

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