Pyridine → HCID 17762557, compound

HRID 583016Notes

Reaction equation

HRID 583016 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].[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1)([O-:22])=[O:21].N1C=CC=CC=1>C(#N)C>[N+:20]([C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:31])[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:27][CH:28]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 179051-OctadecanethiolHCID 66012Benzene, 1-isocyanato-4-nitro-

Product 1

HCID 17762557HCID 17762557, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a three necked flask equipped with a dropping funnel, a thermometer and reflux condenser, n-octadecanethiol (183 g) was dissolved in acetonitrile (1000 ml) in a nitrogen atmosphere. To the solution, p-nitrophenyl isocyanate (100 g) was gradually added and then pyridine (4 ml) was added dropwise, the mixture was stirred at room temperature for 10 minutes and then refluxed for 30 minutes. The reaction mixture was cooled to room temperature to allow crystals to precipitate. The crystals were collected by filtering and washed with acetonitrile, to obtain S-n-octadecyl p-nitrophenylthiocarbamate (272 g) at a yield of 99%.

Workup

  1. customIn a three necked flask equipped with a dropping funnel
  2. temperaturea thermometer and reflux condenser
  3. temperaturerefluxed for 30 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customto precipitate
  6. customThe crystals were collected
  7. filtrationby filtering
  8. washwashed with acetonitrile

Sources & evidence

ORD record
ord-d4af048ef303444eace48e23a666bddd
Source dataset
uspto-grants-1999_07
Patent number
US05928988

Reaction notes

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