Benzoyl isothiocyanate → 1-Benzoyl-3-(3-(benzyloxy)-5-bromopyrazin-2-yl)thiourea

HRID 1426099Notes

Reaction equation

HRID 1426099 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:19][C:20]1[C:21]([NH2:27])=[N:22][CH:23]=[C:24]([Br:26])[N:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[C:1]([NH:9][C:10]([NH:27][C:21]1[C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:25][C:24]([Br:26])=[CH:23][N:22]=1)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 107551623-(Benzyloxy)-5-bromopyrazin-2-amine

Product 1

HCID 866396541-Benzoyl-3-(3-(benzyloxy)-5-bromopyrazin-2-yl)thioureaYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the method of Example 1, Step B, benzoyl isothiocyanate (1.47 g, 8.99 mmol) and 3-(benzyloxy)-5-bromopyrazin-2-amine (2.29 g, 8.18 mmol) were reacted in THF (30 mL) to provide 1-benzoyl-3-(3-(benzyloxy)-5-bromopyrazin-2-yl)thiourea (2.38 g, 66%) as a yellow powder. 1H NMR (CDCl3) δ 8.15 (bs, 1H), 7.91 (d, 2H), 7.66 (t, 1H), 7.53-7.57 (m, 4H), 7.36-7.44 (m, 3H), 5.55 (s, 2H). Mass spectrum (apci) m/z=202 (100), 443 (45), 445 (43) (M+H).

Sources & evidence

ORD record
ord-72511a554824423889cb1d0e835a87db
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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