Water → 4-[4-(4-fluorophenoxy)phenyl]-5-methyl-2-(phenoxymethyl)-1H-imidazole

HRID 493379

반응식

HRID 493379 반응식
Cl.[O:2]([CH2:9][C:10](=[NH:12])[NH2:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].Br[CH:16]([CH3:33])[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[CH:21][CH:20]=1)=O.O>ClCCl.CN(C)C=O.C(OCC)(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][C:22]2[CH:23]=[CH:24][C:19]([C:17]3[N:12]=[C:10]([CH2:9][O:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=4)[NH:11][C:16]=3[CH3:33])=[CH:20][CH:21]=2)=[CH:27][CH:28]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27459122-Phenoxyacetamidine HydrochlorideHCID 860126102-Bromo-1-[4-(4-fluorophenoxy)phenyl]propan-1-one

생성물 1

HCID 114061904-[4-(4-fluorophenoxy)phenyl]-5-methyl-2-(phenoxymethyl)-1H-imidazole

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

620 mg of 2-phenoxyethanimidamide hydrochloride (0.00333 mol) are desalified in dichloromethane by the action of a 3N sodium hydroxide solution. After decantation and extraction of the aqueous phase by dichloromethane, the organic phase is dried over sodium sulphate then evaporated to dryness. The white powder obtained is solubilized in dimethylformamide (30 ml). 275 mg of 2-bromo-1-[4-(4-fluorophenoxy)phenyl]propan-1-one (0.000851 mol) is added. The mixture is heated at 50° C. for 20 hours then returned to 23° C. before adding 25 ml of water and 30 ml of ethyl acetate. After extraction with ethyl acetate, the organic phase is dried over sodium sulphate then evaporated in a rotary evaporator under vacuum. The residue obtained is adsorbed on silica then purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 2-8). A pale yellow-coloured foam is obtained.

후처리

  1. extractionAfter decantation and extraction of the aqueous phase by dichloromethane
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. customthen evaporated to dryness
  4. customThe white powder obtained
  5. customthen returned to 23° C.
  6. extractionAfter extraction with ethyl acetate
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. customthen evaporated in a rotary evaporator under vacuum
  9. customThe residue obtained
  10. customthen purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 2-8)
  11. customA pale yellow-coloured foam is obtained

출처 및 근거

ORD 기록
ord-001b0d8372e0418badf9340602733873
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534805B2

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