Sodium Methoxide → HCID 21303400, compound

HRID 51852Notes

Reaction equation

HRID 51852 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]2[CH2:24][C@@H:23]3[CH2:25][C@H:20]2[CH2:21][O:22]3)[CH:16]=[CH:15][C:14]=1[O:26][CH3:27])=[S:11])(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[CH3:27][O:26][C:14]1[CH:15]=[CH:16][C:17]([N:19]2[CH2:24][C@@H:23]3[CH2:25][C@H:20]2[CH2:21][O:22]3)=[CH:18][C:13]=1[NH:12][C:10]([NH2:9])=[S:11]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 213033971-benzoyl-3-[2-methoxy-5-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-phenyl]-thiourea

Product 1

HCID 21303400HCID 21303400, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of 7.25 g (18.9 mmol) 1-benzoyl-3-[2-methoxy-5-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-phenyl]-thiourea in 350 ml methanol was added dropwise 7.02 ml (37.8 mmol) 5.4 M sodium methylate solution and stirring continued for 1 h at room temperature. The resulting crystals were collected by filtration to afford 3.42 g (65%) [2-methoxy-5-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1 ]hept-5-yl)}-phenyl]-thiourea as a beige solid. ES-MS m/e (%):302 (M+Na+, 20), 281 (M+H+, 100).

Workup

  1. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-48fe6a1748dd4e0c807b86068a0a0f29
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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