2-Bromo-6-phenylcyclohexanone → [4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine

HRID 2076142ノート

反応式

HRID 2076142 の反応式
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([NH2:16])=[S:15])=[CH:9][CH:8]=2)[S:4][N:3]=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>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[S:15][C:26]4[CH2:27][CH2:28][CH2:29][CH:24]([C:20]5[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=5)[C:25]=4[N:16]=3)=[CH:11][CH:12]=2)[S:4][N:3]=1

参加物

4

反応物 2

HCID 127791292-Bromo-6-phenylcyclohexanoneHCID 86632617[4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-thiourea

生成物 1

HCID 44193963[4-(3-Methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-(4-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine収率 10%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of [4-(3-methyl-[1,2,4]thiadiazol-5-yl)-phenyl]-thiourea (75 mg, 0.3 mmol) and 2-bromo-6-phenyl-cyclohexanone (84 mg, 0.33 mmol) in ethanol (3 ml) was heated to reflux over night. The precipitated solid, unreacted thiourea, was filtered off after cooling to room temperature and washed with ethanol. The filtrate was evaporated under reduced pressure and the residue was purified on silica gel using heptane/ethyl acetate (4:1 v/v) as the eluent to yield the title compound (12 mg, 10%) as a yellow solid. MS ISP (m/e): 405.2 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=10.51 (br s, 1H, NH), 7.82 (d, 2H), 7.58 (d, 2H), 7.28 (t, 2H), 7.19 (t, 1H), 7.13 (d, 1H), 4.07 (m, 1H), 2.72 (m, 2H), 2.58 (s, 3H), 2.13 (m, 1H), 1.70-1.90 (m, 3H).

後処理

  1. temperatureto reflux over night
  2. filtrationThe precipitated solid, unreacted thiourea, was filtered off
  3. washwashed with ethanol
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was purified on silica gel

出典と根拠

ORDレコード
ord-32ce4e6f5b844d669585f0e0188f4f2b
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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