Ethylene Glycol → 1-[2,2-Ethylenedioxy-2-(2-naphthyl)ethyl]imidazole

HRID 26540

反応式

HRID 26540 の反応式
Cl.[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)=[O:13].[CH2:20](O)[CH2:21][OH:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:20]1[CH2:21][O:22][C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:2]=2)([CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[O:13]1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 51199Nafimidone monohydrochlorideHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 30541231-[2,2-Ethylenedioxy-2-(2-naphthyl)ethyl]imidazole

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5.45 g. of 1-(2-naphthoylmethyl)imidazole hydrochloride, 2.49 g. ethylene glycol and 7.6 g. p-toluenesulfonic acid monohydrate in 50 ml. of toluene is heated overnight under reflux through a Dean-Stark trap. The trap is then replaced by a separatory funnel containing 4 A molecular seives and heating is continued for a further day. After cooling, the mixture is treated with 200 ml. of ethyl acetate, neutralized by pouring into excess aqueous potassium carbonate and the organic phase separated and dried (MgSO4) to afford a solution of 1-[2,2-ethylenedioxy-2-(2-naphthyl)ethyl]imidazole. The hydrochloride salt is prepared by dropwise addition of ethereal hydrogen chloride until precipitation is complete. Filtration and recrystallization from acetone/methanol gives 3.9 g. pure hydrochloride. m.p. 269°-270° C.

後処理

  1. additionA mixture of 5.45 g
  2. temperatureunder reflux through a Dean-Stark trap
  3. customThe trap is then replaced by a separatory funnel
  4. additioncontaining 4 A molecular seives
  5. temperatureheating
  6. waitis continued for a further day
  7. temperatureAfter cooling
  8. additionthe mixture is treated with 200 ml
  9. customthe organic phase separated
  10. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-f5f7466ae81b4ad3bd899d47583d00e1
出典データセット
uspto-grants-1979_04
特許番号
US04150153

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