Pyridine → HCID 21972242, compound

HRID 1375313Notes

Reaction equation

HRID 1375313 reaction equation
[CH2:1]([SH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N1C=CC=CC=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(#N)C>[C:26]1([NH:32][C:33](=[O:34])[S:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7672Phenyl isocyanateHCID 179051-Octadecanethiol

Product 1

HCID 21972242HCID 21972242, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 15.69 g (54.8 mmol) of octadecanethiol, 250 ml of acetonitrile, and 5 ml (4.9 g, 62 mmol) of pyridine and under a nitrogen atmosphere, 6.52 g (0.54.8 mmol) of phenylisocyanate were added all at once. The mixture was heated to reflux for 2 hours, then cooled to room temperature. The product crystallized, was collected by filtration, and was recrystallized from acetonitrile to give 19.19 g of S-octadecyl phenylcarbamothioate (Compound PS-1), mp 85.5–86.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe product crystallized
  4. filtrationwas collected by filtration
  5. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b043c8d8bc49455d9fbb9972b7217d32
Source dataset
uspto-grants-2007_01
Patent number
US07169543B2

Reaction notes

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