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

HRID 493379

反応式

HRID 493379 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-001b0d8372e0418badf9340602733873
出典データセット
uspto-grants-2009_05
特許番号
US07534805B2

関連ノート

読み込み中…