Iodoethane → HCID 90392793, compound

HRID 1479820Notes

Reaction equation

HRID 1479820 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C@@H:11]([CH2:16][OH:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](I)[CH3:25]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:24][CH3:25])[C@@H:11]([CH2:16][OH:17])[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 90392794HCID 90392794, compound

Product 1

HCID 90392793HCID 90392793, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 5 (10 g, 30 mmol) dissolved in DMF (100 ml) was added with K2CO3 (1.1 equiv., 4.56 g) and ethyl iodide (1.1 equiv., 3.16 ml) and the reaction was stirred at rt overnight. The reaction was diluted with ethyl acetate and washed several times with water and finally with Brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by crystallization from ethyl ether and petroleum ether afforded 10 g of a semisolid. Yield=93%. 1HNMR (DMSO, 200 MHz) δ 1.17 (3H, t, J=7 Hz), 3.40 (2H, q), 3.54 (3H, s), 3.80 (2H, t, J=5.8 Hz), 4.50 (1H, t), 5.00 (1H, bt), 7.28 (1H, dd, J=4 Hz, J′=1 Hz), 7.57 (1H, dd, J=4.2 Hz, J′=1 Hz).

Workup

  1. washwashed several times with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe purification of the crude residue
  5. customby crystallization from ethyl ether and petroleum ether

Sources & evidence

ORD record
ord-bbfdd024265347bbadda61cb1a430072
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

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