Sodium Methoxide → [2-Methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea

HRID 1582105Notes

Reaction equation

HRID 1582105 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[CH:15][C:14]=1[O:25][CH3:26])=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[CH3:26][O:25][C:14]1[CH:15]=[CH:16][C:17]([CH:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 227195711-Benzoyl-3-[2-methoxy-5-(tetrahydropyran-4-yl)-phenyl]-thiourea

Product 1

HCID 22015747[2-Methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thioureaYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3.25 g (8.77 mmol) 1-benzoyl-3-[2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea in 45 ml methanol was added dropwise 0.25 ml (1.32 mmol) 5.3 M sodium methylate solution and stirring continued for 1 h at room temperature. The mixture was then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate) afforded 1.90 g (81%) [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea as a white foam. ES-MS m/e (%): 267 (M+H+, 100).

Workup

  1. additionThe mixture was then poured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90e895e6b1e14a6e955de518f9bd240b
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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