Benzoyl isothiocyanate → 1-Benzoyl-3-(3-iodo-5-methoxy-2-phenyl-pyridin-4-yl)-thiourea

HRID 917461Notes

Reaction equation

HRID 917461 reaction equation
[I:1][C:2]1[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[NH2:8].[C:17]([N:25]=[C:26]=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[C:17]([NH:25][C:26]([NH:8][C:7]1[C:6]([O:9][CH3:10])=[CH:5][N:4]=[C:3]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:2]=1[I:1])=[S:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 589627083-Iodo-5-methoxy-2-phenyl-pyridin-4-ylamine

Product 1

HCID 589626981-Benzoyl-3-(3-iodo-5-methoxy-2-phenyl-pyridin-4-yl)-thioureaYield 67.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 159 g (4.88 mmol) 3-iodo-5-methoxy-2-phenyl-pyridin-4-ylamine in 30 ml acetone was added dropwise 0.98 ml (7.31 mmol) benzoyl isothiocyanate at room temperature. The reaction mixture then heated at reflux for 5 h before being cooled to room temperature concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 1.61 g (67%) 1-benzoyl-3-(3-iodo-5-methoxy-2-phenyl-pyridin-4-yl)-thiourea as a yellow crystalline solid. ES-MS m/e (%): 490 (M+H+, 100).

Workup

  1. temperatureThe reaction mixture then heated
  2. temperatureat reflux for 5 h
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c285e23569df4912a306045aafab36dd
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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