碘化钾 → 1-[(Benzyloxy)methyl]-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

HRID 261973

反应方程式

HRID 261973 反应方程式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[OH:9])=[CH:4][CH:3]=1.[OH-].[Na+].C1(C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1)[N+]([O-])=O.[I-].[K+].[CH2:42]([O:49][CH2:50]Cl)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(#N)C>[CH2:42]([O:49][CH2:50][N:14]1[CH:13]=[CH:12][N:11]=[C:10]1[C:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[OH:9])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

参与物

7

反应物 5

HCID 4875碘化钾HCID 6954苦味酸HCID 14798二甲基对苯二胺二盐酸HCID 137983苄基氯甲基醚HCID 12433870Bis-(4-chloro-phenyl)-(1H-imidazol-2-yl)-methanol

产物 1

HCID 34440691-[(Benzyloxy)methyl]-alpha,alpha-bis(p-chlorophenyl)imidazole-2-methanol

试剂、催化剂与溶剂 1

HCID 6342乙腈溶剂2 次

反应条件

温度
50 °C

实验过程

A mixture of 125 ml. of acetonitrile, 9.2 g of α,α-bis(p-chlorophenyl)imidazole-2-methanol (prepared according to Example III) and 1.5 g of sodium hydroxide was stirred for one hour. To the--now homogeneous--reaction mixture 500 mg of picric acid and a few crystals of potassium iodide were added and the mixture was heated to 50° C. A solution of 5.2 g of benzyloxymethyl chloride in 50 ml. of acetonitrile was then added dropwise and the reaction mixture was subsequently refluxed for 4 hours. The mixture was cooled and filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in water and the suspension was extracted with diethyl ether. The extract was dried over sodium sulphate and the ether was distilled off. The solid residue obtained was crystallized from isopropyl alcohol. The product was then boiled four times with 75 ml. of petroleum ether (boiling range 60°-80° C.), the petroleum ether being decanted each time, after which it was once again crystallized from isopropyl alcohol. The substance was dried in vacuo for 10 hours at 110° C. 1-[(Benzyloxy)methyl]-α,α-bis(p-chlorophenyl)imidazole-2-methanol was obtained. Melting point 139°-141° C.

后处理

  1. additionA mixture of 125 ml
  2. temperaturethe reaction mixture was subsequently refluxed for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. extractionthe suspension was extracted with diethyl ether
  7. dry with materialThe extract was dried over sodium sulphate
  8. distillationthe ether was distilled off
  9. customThe solid residue obtained
  10. customwas crystallized from isopropyl alcohol
  11. customof petroleum ether (boiling range 60°-80° C.), the petroleum ether being decanted each time
  12. customafter which it was once again crystallized from isopropyl alcohol
  13. customThe substance was dried in vacuo for 10 hours at 110° C

来源与证据

ORD记录
ord-dfc1f11540a14a0b9581d3579560ae13
来源数据集
uspto-grants-1979_05
专利号
US04152441

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