Benzoyl chloride → 1-Benzoyl-3-[2-methoxy-5-(tetrahydropyran-4-yl)-phenyl]-thiourea

HRID 2222183Notes

Reaction equation

HRID 2222183 reaction equation
[C:1]([SH:3])#[N:2].N.[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:18][C:17]=1[NH2:28]>CC(C)=O>[C:5]([NH:2][C:1]([NH:28][C:17]1[CH:18]=[C:19]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:20]=[CH:21][C:16]=1[O:15][CH3:14])=[S:3])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 13417437AmthioHCID 219192622-Methoxy-5-(tetrahydropyran-4-yl)-phenylamine

Product 1

HCID 227195711-Benzoyl-3-[2-methoxy-5-(tetrahydropyran-4-yl)-phenyl]-thioureaYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of 1.11 g (14.6 mmol) ammonium rhodanide in 60 ml acetone was added dropwise 1.54 ml (13.3 mmol) benzoyl chloride and the mixture heated at reflux for 10 minutes. A solution of 2.75 g (13.3 mmol) 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine in 30 ml acetone was then added dropwise and the reaction mixture heated at reflux for a further 10 minutes. The mixture was then cooled to room temperature, poured onto sodium bicarbonate solution, and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed by trituration in ether afforded 3.25 g (66%) 1-benzoyl-3-[2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea as a white solid. ES-MS m/e (%): 371 (M+H+, 100).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 10 minutes
  3. temperaturethe reaction mixture heated
  4. temperatureat reflux for a further 10 minutes
  5. additionpoured onto sodium bicarbonate solution
  6. extractionextracted three times with dichloromethane
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2c28496b1374d5ba70bbf58c28fede4
Source dataset
uspto-grants-2008_05
Patent number
US07371748B2

Reaction notes

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