Iodoethane → HCID 90384137, compound

HRID 1479851Notes

Reaction equation

HRID 1479851 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:25][CH3:26]>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:25][CH3:26])[C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 90384238HCID 90384238, compound

Product 1

HCID 90384137HCID 90384137, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 16 (2 g, 6.7 mmol) in DMF (20 mL) was added with an. K2CO3 (1.5 mol eq, 1.4 g) and, after few minutes, 2-iodoethane (1.2 mol eq, 0.84 ml) was added and the mixture was heated at 50° C. for 4 h. The solvent was removed under reduced pressure, water was added to the residue (100 mL) and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 17 as a pale yellow oil (2.1 g, 95% yield). 1HNMR (DMSO, 200 MHz) δ 1.18 (m, 2H), 1.25 (t, 3H), 1.37 (m, 2H), 1.98 (s, 3H), 3.45 (m, 2H), 7.28 (d, 1H, J=4), 7.78 (d, 1H, J=3.9)

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue (100 mL)
  3. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e2916aad70224f9b908f3aa49266ddae
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

Loading…