Hexadecanethiol → S-n-hexadecyl p-nitrophenylthiocarbamate

HRID 583015Notes

Reaction equation

HRID 583015 reaction equation
[CH2:1]([SH:17])[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][CH3:16].[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(#N)C>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:28](=[O:29])[S:17][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][CH3:16])=[CH:25][CH:26]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 18015HexadecanethiolHCID 66012Benzene, 1-isocyanato-4-nitro-

Product 1

HCID 17762555S-n-hexadecyl p-nitrophenylthiocarbamateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a three necked flask equipped with a dropping funnel, a thermometer and reflux condenser, n-hexadecanethiol (165 g) was dissolved in acetonitrile (1000 ml) in a nitrogen atmosphere. To the solution, p-nitrophenyl isocyanate (100 g) was gradually added, stirred at room temperature for 10 minutes, and then heat-refluxed for 30 minutes. The reaction liquid was cooled to room temperature to allow crystals to precipitate. The crystals were collected by filtering and washed with acetonitrile, to obtain S-n-hexadecyl p-nitrophenylthiocarbamate (250 g) at a yield of 97%.

Workup

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

Sources & evidence

ORD record
ord-c299eda7db9b4283bf2016743ef4e09b
Source dataset
uspto-grants-1999_07
Patent number
US05928988

Reaction notes

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