Dichloromethane → HCID 22130469, 화합물

HRID 1416052

반응식

HRID 1416052 반응식
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)=[C:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.[N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[C:32]([CH2:40]Br)[CH:31]=1.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][CH2:9][C:10]1[N:14]([CH2:40][C:32]2[CH:31]=[N:30][C:39]3[C:34]([CH:33]=2)=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:13]([CH:15]([CH3:17])[CH3:16])=[C:12]([S:18][C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=2)[N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 235103313-(Bromomethyl)quinolineHCID 1784190342-Benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole

생성물 1

HCID 22130469HCID 22130469, 화합물수율 2.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In tetrahydrofuran (10 ml)was dissolved 245 mg (2 mmol) of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (101a). To this solution, a methylene chloride solution of quinolin-3-ylmethylbromide was added at room temperature with stirring, followed by addition of 200 mg (5 mmol)of sodium hydroxide and 39 mg (0.12 mmol)of n-tetrabutylammonium bromide. After stirring for 2 hours, the mixture was left overnight and worked up. The reaction mixture was distilled off under reduced pressure. The residue was extracted with methylene chloride, and the extract was washed with water and dried. The solvent was distilled off, and the residual oil was purified by silica gel column chromatography (methylene chloride-ethyl acetate). As the first eluate, 26 g (2.6%)of 2-benzyloxymethyl-4-(3,5-dichlorophenylthio)-5-isopropyl-1-(quinolin-3-ylmethyl)-1H-imidazole (100a)was obtained. From the subsequent eluate, 730 mg of 2-benzyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(quinolin-3-ylmethyl)-1H-imidazole (100b)suited to the next step of the reaction was obtained (yield 73%). mp 95-98° C.

후처리

  1. stirringAfter stirring for 2 hours
  2. distillationThe reaction mixture was distilled off under reduced pressure
  3. extractionThe residue was extracted with methylene chloride
  4. washthe extract was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe residual oil was purified by silica gel column chromatography (methylene chloride-ethyl acetate)

출처 및 근거

ORD 기록
ord-cdf5b90a6b1a4c51be9d5d854a1bed97
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05910506

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