Iodoethane → HCID 131736593, compound

HRID 1479843Notes

Reaction equation

HRID 1479843 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH:17]([OH:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26](I)[CH3:27]>CN(C=O)C.C(OCC)(=O)C>[CH2:26]([N:11]([S:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)(=[O:9])=[O:10])[C@@H:12]([CH:17]([OH:19])[CH3:18])[C:13]([O:15][CH3:16])=[O:14])[CH3:27]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 131736594HCID 131736594, compound

Product 1

HCID 131736593HCID 131736593, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 9C (3 g, 8.94 mmol) dissolved in DMF (15 ml) was added with K2CO3 (1.1 equiv., 1.36 g) and ethyl iodide (1.1 equiv., 1 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 2.8 g of a semisolid. Yield=97%. 1HNMR (DMSO, 200 MHz) δ 1.00 (3H, d, J=6.2 Hz), 1.26 (3H, t, J=7 Hz), 3.32 (3H, s), 3.34 (2H, m), 4.02 (1H, bs), 4.23 (1H, m), 5.14 (1H, d, J=4.4 Hz), 7.62 (2H, m), 7.76 (2H, m)

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-0135972efecc4cc4ac1bc64175b9adc5
Source dataset
uspto-grants-2016_08
Patent number
US09409864B2

Reaction notes

Loading…