Benzyl Chloride → HCID 44295815, compound

HRID 1449603Notes

Reaction equation

HRID 1449603 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])[CH:7]=1.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:17]([S:15][C:9]1[N:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[CH3:16])[C:12](=[O:13])[CH2:11][N:10]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 53995114HCID 53995114, compound

Product 1

HCID 44295815HCID 44295815, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-[3-(5-chloro-2-methylphenyl)-thioureido]-acetamide (20.6 g), benzyl chloride (25.0 g), and ethanol (350 mL) was heated at reflux for 2.5 hours. The insolubles were removed by filtration and discarded. The filtrate was concentrated to one-half volume. Diethyl ether (300 mL) was added. The precipitated solid was separated by filtration and discarded. The filtrate was evaporated to dryness. The residue was dissolved in chloroform (300 mL) and washed with water. The organic phase was dried over anhydrous MgSO4, decolorized on carbon then evaporated to dryness. The residue was triturated with diethyl ether to give the title compound (14.2 g) as an off-white solid, m.p. 140°-142° C. Anal. Calcd. for. C17H15Cl N2O S: C, 61.72; H, 4.57; N, 8.47. Found: C, 61.62; H, 4.39; N, 8.37. Mass spectrum (EI, M.+) m/z 330/332. 1H-NMR (DMSO-d6 ; 400 MHz) δ7.46 (m, 1H), 7.42 (m, 2H), 7.38 (d, 2H), 7.22-7.32 (m, 3H), 4.31-4.48 (m, 4H), and 2.06 ppm (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. customThe insolubles were removed by filtration
  4. concentrationThe filtrate was concentrated to one-half volume
  5. additionDiethyl ether (300 mL) was added
  6. customThe precipitated solid was separated by filtration
  7. customThe filtrate was evaporated to dryness
  8. dissolutionThe residue was dissolved in chloroform (300 mL)
  9. washwashed with water
  10. dry with materialThe organic phase was dried over anhydrous MgSO4
  11. customthen evaporated to dryness
  12. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-f50993548453478f8463eb99b0fbee34
Source dataset
uspto-grants-1997_02
Patent number
US05599829

Reaction notes

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