Methyl Isocyanate → N-triphenylmethyl-2-methylaminocarbonylthioethylamine

HRID 1607102Notes

Reaction equation

HRID 1607102 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[C:5]1([C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:12][CH2:13][CH2:14][SH:15])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[C:5]1([C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:12][CH2:13][CH2:14][S:15][C:3]([NH:2][CH3:1])=[O:4])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 15616512N-triphenylmethylcysteamine

Product 1

HCID 15616514N-triphenylmethyl-2-methylaminocarbonylthioethylamineYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methylisocyanate (243 mg) was dissolved in anhydrous dichloromethane (5 ml). To the solution were added N-triphenylmethylcysteamine (3.19 g: 0.33 equimolar amount) while cooling with ice. The reaction solution was stirred at room temperature for 4 hours and was concentrated under reduced pressure. The residue was dissolved in chloroform (50 ml), and the chloroform solution was well washed with water and a saturated solution of sodium chloride. Anhydrous sodium sulate was used to dry the chloroform layer which was then concentrated under reduced pressure. The residue was purified by silica gel chromatography using a solvent system of hexane/ethyl acetate (5:1 v/v) to obtain the desired substance (297 mg) with a yield of 79%.

Workup

  1. temperaturewhile cooling with ice
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform (50 ml)
  4. washthe chloroform solution was well washed with water
  5. dry with materialto dry the chloroform layer which
  6. concentrationwas then concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. customto obtain the desired substance (297 mg) with a yield of 79%

Sources & evidence

ORD record
ord-88a1850dfd1e43d28f014436e301362c
Source dataset
uspto-grants-1989_09
Patent number
US04863935

Reaction notes

Loading…