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

HRID 337569
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HRID 337569 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 3283
Diethyl Ether
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0f2800fc9c6d4971b08ad0dff9b78bee
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889714B2

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