1,1-Dichloroethane → HCID 67065316, compound

HRID 1506674Notes

Reaction equation

HRID 1506674 reaction equation
[CH:1]1([NH:7][C:8](=[O:28])[CH2:9][C:10]2[CH:15]=[C:14]([I:16])[C:13]([O:17][C:18]3[CH:23]=[C:22]([I:24])[C:21]([OH:25])=[C:20]([I:26])[CH:19]=3)=[C:12]([I:27])[CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:35][CH:36](Cl)[CH3:37]>>[Cl:35][CH2:36][CH2:37][O:25][C:21]1[C:22]([I:24])=[CH:23][C:18]([O:17][C:13]2[C:14]([I:16])=[CH:15][C:10]([CH2:9][C:8]([NH:7][CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[O:28])=[CH:11][C:12]=2[I:27])=[CH:19][C:20]=1[I:26]

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 10796Cesium carbonateHCID 67065315HCID 67065315, compound

Product 1

HCID 67065316HCID 67065316, compoundYield 5%

Procedure

Compound 4 (2.0 g, 2.1 mmol, 1.0 eq.) was dissolved in anhydrous dichloroethane (30 mL) and then Cs2CO3 (1.7 g, 5.2 mmol, 2.5 eq.) was added. The reaction medium was then slowly heated to reflux. The mixture was stirred for 12 hrs. upon reflux then cooled to room temperature, filtered and the solvent was removed under vacuum. The residual oil then was purified by column chromatography (DCM/hexanes 80/20). The product was further recrystallized to give 2-(4-(4-(2-chloroethoxy)-3,5-diiodophenoxy)-3,5-diiodophenyl)-N-cyclohexylacetamide, compound 15, (94 mg, 0.1 mmol) as a powder.

Workup

  1. temperatureThe reaction medium was then slowly heated to reflux
  2. temperatureupon reflux
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum
  5. customThe residual oil then was purified by column chromatography (DCM/hexanes 80/20)
  6. customThe product was further recrystallized

Sources & evidence

ORD record
ord-f74d3c9a2da24e13be724d3887ae2d88
Source dataset
uspto-grants-2015_12
Patent number
US09220788B2

Reaction notes

Loading…