Sodium Methoxide → {2-Methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea

HRID 51891Notes

Reaction equation

HRID 51891 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]([CH3:27])[CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:16]=[CH:15][C:14]=1[O:28][CH3:29])=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[CH3:29][O:28][C:14]1[CH:15]=[CH:16][C:17]([N:19]([CH3:27])[CH2:20][CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 227369731-Benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea

Product 1

HCID 22736994{2-Methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thioureaYield 101%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 2.0 g (4.8 mmol) 1-benzoyl-3-{2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea in 15 ml methanol was added dropwise 0.4 ml (7.25 mmol) 5.4 M sodium methylate solution and stirring continued for 18 hrs at room temperature. The mixture was then concentrated in vactio and the residue subjected to column chromatography (1/1 hexane/ethyl acetate) to afford 1.5 g (100%) {2-methoxy-5-[methyl-(tetrahydro-pyran-4-ylmethyl)-amino]-phenyl}-thiourea as a beige oil. ES-MS m/e (%): 310 (M+H+, 100).

Workup

  1. concentrationThe mixture was then concentrated in vactio

Sources & evidence

ORD record
ord-572bbe088c8e44a5b8281fd00d663dbd
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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