Triethylamine → 1-Tert-butyl-4-(isothiocyanatomethyl)benzene

HRID 656261Notes

Reaction equation

HRID 656261 reaction equation
C1C=C(O[C:8](OC2N=CC=CC=2)=[S:9])N=CC=1.[C:17]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:26]=[C:8]=[S:9])=[CH:27][CH:28]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 719784O,O-Dipyridin-2-yl carbonothioateHCID 27356554-tert-Butylbenzylamine

Product 1

HCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzeneYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Di-2-pyridyl thionocarbonate (45 mg) was dissolved in methylenechloride (2 ml) and to the solution were added 4-t-butylbenzylamine (29 mg) and triethylamine (20 μl), followed by stirring at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure and the obtained residue was chromatographed on a silica gel column eluting with ethyl acetate/hexane (1/10) to yield 4-t-butylbenzylisothiocyanate (26 mg, 71%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was chromatographed on a silica gel column
  3. washeluting with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-56c87bf4b0574d14905371ba19e6190f
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

Loading…