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

HRID 337569Notes

Reaction equation

HRID 337569 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0f2800fc9c6d4971b08ad0dff9b78bee
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…