1-Tert-butyl-4-(isothiocyanatomethyl)benzene → 1-(4-t-butylbenzyl)-3-(1H-pyrrol-2-ylmethyl)thiourea

HRID 656286Notes

Reaction equation

HRID 656286 reaction equation
Cl.[NH:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][NH2:8].[C:9]([C:13]1[CH:22]=[CH:21][C:16]([CH2:17][N:18]=[C:19]=[S:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>ClCCl>[C:9]([C:13]1[CH:22]=[CH:21][C:16]([CH2:17][NH:18][C:19]([NH:8][CH2:7][C:3]2[NH:2][CH:6]=[CH:5][CH:4]=2)=[S:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 148010411-Tert-butyl-4-(isothiocyanatomethyl)benzeneHCID 56763810(1H-Pyrrol-2-yl)methanamine hydrochloride

Product 1

HCID 590880561-(4-t-butylbenzyl)-3-(1H-pyrrol-2-ylmethyl)thioureaYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1H-pyrrol-2-yl)methylamine hydrochloride (60 mg) prepared according to the same procedure as described in Step 2 was dissolved in dichloromethane (2 ml) and to the solution was added 4-t-butylbenzylisothiocyanate (155 mg), followed by stirring at room temperature for 1 hour. The resulting mixture was concentrated under reduced pressure and the obtained residue was column-chromatographed (ethyl acetate/hexane=1/3) to yield the compound 17-1 (120 mg, 65%).

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customthe obtained residue was column-chromatographed (ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-19adcc77da7b433e866fa70e92d7f10e
Source dataset
uspto-grants-2011_12
Patent number
US08071650B2

Reaction notes

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