Triethylamine → 2-(Methylthio)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid Phenyl Ester

HRID 18839

反応式

HRID 18839 の反応式
I.[C:2]1([C@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:11][C:10]([S:19][CH3:20])=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:30]>CN(C)C1C=CN=CC=1.ClCCl>[C:32]1([O:31][C:29]([N:9]2[C@H:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C@H:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:11]=[C:10]2[S:19][CH3:20])=[O:30])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 68569083cis-4,5-Diphenyl-2-methylthio-4,5-dihydro-1H-imidazole hydroiodide

生成物 1

HCID 596554592-(Methylthio)-cis-4,5-diphenyl-4,5-dihydro-imidazole-1-carboxylic Acid Phenyl Ester収率 59.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(methylthio)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydroiodide (42) (1.00 mg, 2.52 mmol), triethylamine (0.528 mL, 0.379 mmol), 4-dimethylamino-pyridine (10 mg) in dichloromethane (20 mL) is added phenyl chloroformate (0.379 mL, 3.02 mmol), and the mixture is stirred at rt overnight. The reaction mixture is diluted with dichloromethane and washed with water, brine, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 0.58 g of the product 548. 1H NMR (CDCl3) δ 7.25-6.95 (m, 11H), 6.95-6.80 (m, 2H), 6.80-6.70 (m, 2H), 5.80-5.65 (m, 2H), 2.62 (s, 3H). MS: m/z 389 (M++1).

後処理

  1. washwashed with water, brine
  2. dry with materialthe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on silica gel
  6. washgradient elution with heptane:EtOAc (70:30-60:40)

出典と根拠

ORDレコード
ord-38f7a9f155714a62b76115b2a7142ad9
出典データセット
uspto-grants-2010_06
特許番号
US07741493B2

関連ノート

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