Iodoethane → HCID 87546601, compound

HRID 1435691Notes

Reaction equation

HRID 1435691 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([CH3:22])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][OH:21])[N:18]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[CH2:23](I)[CH3:24]>O1CCCC1>[Cl:3][C:4]1[C:5]([CH3:22])=[C:6]([S:10]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH2:19][CH2:20][O:21][CH2:23][CH3:24])[N:18]=2)(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 87545745HCID 87545745, compound

Product 1

HCID 87546601HCID 87546601, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (95% dry, 80 mg, 3.23 mmol) was added to a stirred solution of EXAMPLE 181A (426 mg, 1.28 mmol) in tetrahydrofuran (10 mL) at room temperature. After stirring for 15 min, the mixture was treated with ethyl iodide (400 mg, 2.56 mmol). The reaction mixture was stirred for 2 h at 55° C. and then quenched with aqueous HCl (1 M, 1 mL) and water was added. The product was extracted with DCM and dried (Sodium sulfate). Evaporation of the solvent gave a residue which was purified by flash chromatography on silica gel eluting with 10% acetone in DCM giving an oil (0.25 g, 54%) which solidified on standing: MS (Ionspray, [M+H]+) m/z 360; Anal. Calcd. (found) for C14H17ClN2O3S2: C, 46.6 (46.5)%; H, 4.7 (4.6)%; N, 7.8 (7.8)%.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at 55° C.
  2. customquenched with aqueous HCl (1 M, 1 mL) and water
  3. additionwas added
  4. extractionThe product was extracted with DCM
  5. dry with materialdried (Sodium sulfate)
  6. customEvaporation of the solvent
  7. customgave a residue which
  8. customwas purified by flash chromatography on silica gel eluting with 10% acetone in DCM giving an oil (0.25 g, 54%) which

Sources & evidence

ORD record
ord-71100907b9134f029d244bff2f8d63d0
Source dataset
uspto-grants-2009_11
Patent number
US07618961B2

Reaction notes

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