Hydrochloric Acid → (5-Methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea

HRID 917409Notes

Reaction equation

HRID 917409 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+].Cl>O1CCCC1.CO>[CH3:20][O:19][C:18]1[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[CH:14][C:15]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:16][CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 589626971-Benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea

Product 1

HCID 58962702(5-Methoxy-2-morpholin-4-yl-pyridin-4-yl)-thioureaYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5.80 g (15.6 mmol) 1-benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea in 100 ml tetrahydrofuran and 25 ml methanol heated at 60° C. was added dropwise 1.15 ml (6.23 mmol) 5.4 M sodium methylate solution and stirring continued for 2 h at 60° C. 1.2 ml concentrated hydrochloric acid was then added and the reaction mixture concentrated in vacuo. The residue was triturated in 25 ml ether to afford 3.51 g (84%) (5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea as alight brown crystalline solid. ES-MS m/e (%): 269 (M+H+, 100).

Workup

  1. concentrationthe reaction mixture concentrated in vacuo
  2. customThe residue was triturated in 25 ml ether

Sources & evidence

ORD record
ord-6e651137d2d841cfa1aa6b1b4276a272
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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