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Sodium Iodide → 1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(cyanomethyl)phenyl]methyl}carbamate

HRID 337569
ノート
印刷プレビュー

反応式

HRID 337569 の反応式
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][N:14]([CH:22]2[CH2:24][CH2:23]2)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([Cl:25])=[C:9]([Cl:26])[CH:8]=1)(=O)=O.[C-:27]#[N:28].[K+].[I-].[Na+]>CS(C)=O.CCOCC>[CH:22]1([N:14]([CH2:13][C:11]2[CH:12]=[C:7]([CH2:6][C:27]#[N:28])[CH:8]=[C:9]([Cl:26])[C:10]=2[Cl:25])[C:15](=[O:16])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:24][CH2:23]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5238Sodium IodideHCID 9032Potassium CyanideHCID 86651664{3,4-Dichloro-5-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}methyl methanesulfonate

生成物 1

HCID 668962721,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(cyanomethyl)phenyl]methyl}carbamate

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 3283
Diethyl Ether
溶媒

実験手順

To a solution of {3,4-dichloro-5-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}methyl methanesulfonate (1 eq.) from the previous step in DMSO (0.48 M) was added potassium cyanide (1.3 eq.) and sodium iodide (0.1 eq.). The resulting solution was stirred at RT for 3 h before it was diluted with ether and quenched with 1 N aq. NaOH. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

後処理

  1. customquenched with 1 N aq. NaOH
  2. customThe aqueous layer was separated
  3. extractionback-extracted with ether
  4. washThe combined organic extracts were washed further with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

出典と根拠

ORDレコード
ord-0f2800fc9c6d4971b08ad0dff9b78bee
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889714B2

反応ノート

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