Benzyl Isothiocyanate → 1-Benzyl-3-(5-cyano-2-ethylaminophenyl)thiourea

HRID 600821Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH3:12])[C:5]#[N:6].[CH2:13]([N:20]=[C:21]=[S:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([NH:20][C:21]([NH:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH3:12])=[S:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 3-amino-4-ethylamino-benzonitrile (1.0 g, 6.2 mmol) in THF (50 mL, anhyd) was added benzylisothiocyanate (0.92 g, 6.2 mmol). The reaction mixture was heated at 50° C. with stirring. After 6 h, the reaction mixture was cooled, concentrated under reduced pressure, and chromatographed (silica gel, 1:1 EtOAc/Hex) to yield 1-benzyl-3-(5-cyano-2-ethylaminophenyl)thiourea (1.78 g, 93%). 1H-NMR (CDCl3): δ 7.48 (1H, dd), 7.37 (1H, d), 7.31 (3H, m), 7.24 (1H, s), 7.18 (1H, br), 6.67 (1H, d), 5.95 (1H, br), 4.81 (2H, d), 4.68 (1H, br), 3.19 (2H, m), 1.23 (3H, t).

Workup

temperaturethe reaction mixture was cooled
concentrationconcentrated under reduced pressure
customchromatographed (silica gel, 1:1 EtOAc/Hex)

Sources & evidence

ORD record: ord-56bd1b5c31104487b01759f1630e58b2
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902237B2

Reaction notes

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