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Iodoethane → HCID 131736595, compound

HRID 1479848
Notes
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Reaction equation

HRID 1479848 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:25](I)[CH3:26]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:25][CH3:26])[C:12]2([C:15]([O:17][CH3:18])=[O:16])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 90384259HCID 90384259, compound

Product 1

HCID 131736595HCID 131736595, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

Compound 13B (800 mg, 2.76 mmol) dissolved in DMF (10 ml) was added with K2CO3 (1.1 equiv., 420 mg) and ethyl iodide (1.1 equiv., 0.3 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 750 mg of 14B as a semisolid. Yield=85.5%. 1HNMR (DMSO, 200 MHz) δ 1.096 (3H, t, J=7.2 Hz), 1.17 (2H, m), 1.43 (2H, bs), 3.34 (2H, m), 3.43 (3H, s), 7.68 (2H, m), 7.79 (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-2e4653e2c60e4801abc79c5b0d35e1b7
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09409864B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes