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

HRID 1426167Notes

Reaction equation

HRID 1426167 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]([NH2:34])=[N:22][CH:23]=[C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[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:34][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][C:24]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])=[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 673705813-(Benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine

Product 1

HCID 866397001-Benzoyl-3-(3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-yl)thioureaYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoyl isothiocyanate (0.330 g, 2.02 mmol) was added to a solution of 3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-amine (0.660 g, 2.02 mmol) in THF (4 mL). The reaction mixture was stirred for 2 hours at room temperature, diluted with hexanes, filtered, and washed with hexanes to afford 1-benzoyl-3-(3-(benzyloxy)-5-(2-chlorophenoxy)pyridin-2-yl)thiourea (0.92 g, 93.0% yield) as a light yellow powder. 1H NMR (CDCl3) δ 5.16 (s, 2H), 6.95 (s, 1H), 7.00-8.04 (m, 17H).

Workup

  1. filtrationfiltered
  2. washwashed with hexanes

Sources & evidence

ORD record
ord-428134ef3ee14ac389190ad31e5469ea
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

Loading…