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

HRID 1426084Notes

Reaction equation

HRID 1426084 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]([NH2:26])=[N:22][CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[C:1]([NH:9][C:10]([NH:26][C:21]1[C:20]([O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:25][CH:24]=[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 903342-Amino-3-benzyloxypyridine

Product 1

HCID 727056381-Benzoyl-3-(3-(benzyloxy)pyridin-2-yl)thioureaYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 L round-bottomed flask was charged with benzoyl isothiocyanate (22.4 g, 137 mmol), 3-(benzyloxy)pyridin-2-amine (25 g, 125 mmol), and THF (200 mL). The reaction mixture was stirred at room temperature for 2 hours and the diluted with hexanes to 1 L, and then filtered to afford 1-benzoyl-3-(3-(benzyloxy)pyridin-2-yl)thiourea (44.4 g, 97.9% yield) as a yellow solid. 1H NMR (CDCl3) δ 9.00 (m, 1H), 8.08 (m, 1H), 7.87 (m, 1H), 7.62 (m, 1H), 7.54 (m, 2H), 7.41 (m, 5H), 7.27 (m, 1H), 7.02 (m, 1H), 5.22 (s, 2H). LCMS (25 to 95) Rt=2.64 min, (apci) m/z=201, 364 (M+H).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-fc525dd7e96a4e5497e83af55e58a3f9
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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