2-Methoxyphenyl Isothiocyanate → 1-(3-Bromo-pyridin-2-yl)-3-(2-methoxy-phenyl)-thiourea

HRID 472272Notes

Reaction equation

HRID 472272 reaction equation
[Br:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[N:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])=[C:10]=[S:11]>>[Br:1][C:2]1[C:3]([NH:8][C:10]([NH:9][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])=[S:11])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 5205992-Methoxyphenyl IsothiocyanateHCID 8177002-Amino-3-bromopyridine

Product 1

HCID 866483521-(3-Bromo-pyridin-2-yl)-3-(2-methoxy-phenyl)-thiourea

Procedure

1-(3-Bromo-pyridin-2-yl)-3-(2-methoxy-phenyl)-thiourea was prepared from 3-bromo-pyridin-2-ylamine (5.0 g, 29.0 mmol) and 1-isothiocyanato-2-methoxy-benzene (4.0 mL, 29.0 mmol) in a manner analogous to Step 19a. The reaction product was isolated as a yellow solid (8.46 g, 86%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 13.62 (br s, 1H), 8.75-8.65 (m, 2H), 8.21 (dd, J=5.1, 1.5 Hz, 1H), 7.91 (dd, J=8.0, 1.6, Hz, 1H), 7.21 (dt, J=7.9, 1.5 Hz, 1H), 7.06-7.00 (m, 1H), 6.98-6.94 (m, 1H), 6.91 (dd, J=7.9, 5.0 Hz, 1H), 3.93 (s, 3H). MS=340 (MH)+.

Sources & evidence

ORD record
ord-7bd8ddb831ac488dadab198e41fc09c8
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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