Iodoethane → HCID 44295520, compound

HRID 1449596Notes

Reaction equation

HRID 1449596 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])=[CH:4][CH:3]=1.[CH2:16](I)[CH3:17]>C(O)C>[CH2:16]([S:15][C:9]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:12](=[O:13])[CH2:11][N:10]=1)[CH3:17]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 53840358HCID 53840358, compound

Product 1

HCID 44295520HCID 44295520, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(4-fluorophenyl)-thioureido]-acetamide (9.1 g) and ethyl iodide (12.5 g) was heated at reflux in ethanol (200 mL) for 4 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) then washed with water. The organic phase was extracted with 2N HCl (2×400 mL). The acid extract was made basic with 5% sodium bicarbonate solution. The precipitate was collected by filtration and dried. Crystallization from diethyl ether afforded the title compound (2.85 g) as an off-white solid, m.p. 114°-115° C. Anal. Calcd. for. C11H11F N2O S: C, 55.45; H, 4.65; N, 11.76. Found: C, 55.17; H, 4.54; N, 11.81. Mass spectrum (EI, M.+) m/z 238. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.32-7.39 (m, 4H), 4.30 (s, 2H), 3.07 (q, 2H), and 1.28 ppm (t, 3H).

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
  4. washthen washed with water
  5. extractionThe organic phase was extracted with 2N HCl (2×400 mL)
  6. extractionThe acid extract
  7. filtrationThe precipitate was collected by filtration
  8. customdried
  9. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-0deb947b20bd4ccf99bb7d2dd29b67e6
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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