Water → HCID 11162583, compound

HRID 350343Notes

Reaction equation

HRID 350343 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N12CCN(CC1)CC2.[CH3:17][N:18]([CH3:22])[C:19](Cl)=[S:20].O>CN(C=O)C>[CH3:17][N:18]([CH3:22])[C:19](=[S:20])[O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9237DabcoHCID 108944-IodophenolHCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 11162583HCID 11162583, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a stirred solution of p-iodophenol (20.0 g, 90.9 mmol) in DMF (200 mL) was added 1,4-diazabicyclo[2,2,2]octane (20.4 g, 181.8 mmol) and dimethylthiocarbamoyl chloride (16.9 g, 136.4 mmol). The resulting solution was stirred for 3.5 hr at 75° C. After cooling, 300 mL of water was added. The solid was collected with suction and was dissolved in EtOAc. The EtOAc layer was washed with water, dried over Na2SO4, and evaporated under a reduced pressure. The crude solid was recrystallized from H2O to give the 26.75 g (96%) O-p-iodophenyl dimethylthiocarbamate as a pale a yellow crystalline powder. IR (KBr) 1479, 1207, 827 cm−1; 1H-NMR (400 MHz, CDCl3) δ 3.37 (s, 3H), 3.45 (s, 3H), 6.83 (d, J=8.8 Hz, 2H), 7.69 (d, J=8.3 Hz, 2H); MS (FAB) m/z 307 (M++1); Anal. Calcd for C9H10INOS: C, 35.19; H, 3.28; N, 4.56. Found: C, 35.17; H, 3.35; N, 4.44.

Workup

  1. temperatureAfter cooling
  2. customThe solid was collected with suction
  3. dissolutionwas dissolved in EtOAc
  4. washThe EtOAc layer was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under a reduced pressure
  7. customThe crude solid was recrystallized from H2O

Sources & evidence

ORD record
ord-096d2fc4ab3643d98840b6662d173b54
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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