3-(Diethylamino)propyl isothiocyanate → N'-[3-(Diethylamino)propyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]thiourea

HRID 745186

Reaction equation

HRID 745186 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:16]([N:18]([CH2:21][CH2:22][CH2:23][N:24]=[C:25]=[S:26])[CH2:19][CH3:20])[CH3:17]>C(#N)C>[CH2:19]([N:18]([CH2:16][CH3:17])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[S:26])[N:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[CH3:20]

Participants

4

Reactant 2

HCID 27582403-(Diethylamino)propyl isothiocyanateHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

Product 1

HCID 13655152N'-[3-(Diethylamino)propyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]thioureaYield 76.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5.0 g (0.022 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine and 4.30 g (0.025 mole) of 3-(N,N-diethylamino)propylisothiocyanate in 400 ml of acetonitrile was refluxed for 16 hr. The solvent was removed in vacuo and the residue was dissolved in ether. The solution was extracted with three portions of water and was dried over magnesium sulfate. The volume of the ether solution was reduced to 200 ml, and hexane was added until the solution became slightly cloudy. A white solid precipitated to give 6.76 g (76.9%) of white crystalline solid, m.p. 120°-121° C.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ether
  3. extractionThe solution was extracted with three portions of water
  4. dry with materialwas dried over magnesium sulfate
  5. additionwas added until the solution
  6. customA white solid precipitated

Sources & evidence

ORD record
ord-91a18e96e5dc466494837ac45fa13f6b
Source dataset
uspto-grants-1986_07
Patent number
US04597902

Linked notes

Loading…