Sodium Methoxide → {2-Methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea

HRID 51842

Reaction equation

HRID 51842 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]([CH2:21][CH2:22][O:23][CH3:24])[CH3:20])[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]([N:19]([CH2:21][CH2:22][O:23][CH3:24])[CH3:20])=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 220157361-Benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea

Product 1

HCID 22015743{2-Methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thioureaYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 2.00 g (5.36 mmol) 1-benzoyl-3-{2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea in 13 ml methanol was added dropwise 0.15 ml (0.80 mmol) 5.4 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 1.40 g (97%) {2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea as an amber oil. ES-MS m/e (%): 270 (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-1ea0648519114dda86f440fe12a9734a
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Linked notes

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