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

HRID 18839

반응식

HRID 18839 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-38f7a9f155714a62b76115b2a7142ad9
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741493B2

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