Benzoyl isothiocyanate → 1-Benzoyl-3-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea

HRID 1809579Notes

Reaction equation

HRID 1809579 reaction equation
[O:1]([C:8]1[C:9]([NH2:21])=[N:10][CH:11]=[C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:22]([NH:30][C:31]([NH:21][C:9]1[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][C:12]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:11][N:10]=1)=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 669951573-Phenoxy-5-(pyridin-2-ylthio)pyridin-2-amine

Product 1

HCID 866410891-Benzoyl-3-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thioureaYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 125 mL flask was charged with 3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-amine (Example 34, Step A, 1.15 g, 3.89 mmol) and benzoyl isothiocyanate (0.699 g, 4.28 mmol) in THF (50 mL) and stirred at ambient temperature for 18 hours. The THF was removed in vacuo and the residue was dissolved in CH2Cl2 (10 mL) and added dropwise to 100 mL of 9:1 hexanes:EtOAc. The solvent was decanted and the residue was dried to provide 1-benzoyl-3-(3-phenoxy-5-(pyridin-2-ylthio)pyridin-2-yl)thiourea (1.57 g, 88.2% yield) as a yellow solid.

Workup

  1. customThe THF was removed in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  3. additionadded dropwise to 100 mL of 9:1 hexanes
  4. customThe solvent was decanted
  5. customthe residue was dried

Sources & evidence

ORD record
ord-5c284c46d08b40ebbd9b6b0fedaac801
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…