Hexane → 1-Benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea

HRID 917408Notes

Reaction equation

HRID 917408 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:15])=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>CC(C)=O>[C:16]([NH:24][C:25]([NH:15][C:4]1[C:3]([O:2][CH3:1])=[CH:8][N:7]=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=1)=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 68284Benzoyl isothiocyanateHCID 589627015-Methoxy-2-morpholin-4-yl-pyridin-4-ylamine

Product 1

HCID 589626971-Benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thioureaYield 66.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 27.5 g (132 mmol) 5-methoxy-2-morpholin-4-yl-pyridin-4-ylamine in 400 ml acetone was added dropwise 19.5 ml (145 mmol) benzoyl isothiocyanate at room temperature. The reaction mixture then heated at reflux for 90 min before being cooled to room temperature and poured onto 400 ml hexane and stirred for 5 min. The resulting crystals were collected by filtration, washed with hexane and dried to afford 32.5 g (66%) 1-benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea as a brown crystalline solid. ES-MS m/e (%): 373 (M+H+, 100).

Workup

  1. temperatureThe reaction mixture then heated
  2. temperatureat reflux for 90 min
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-016163aaed7b4acf890e68d293f20667
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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