Water → HCID 16073902, compound

HRID 1068017Notes

Reaction equation

HRID 1068017 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21]Cl)[CH:17]=3)[N:12]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:32][S-:33].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][S:33][CH3:32])[CH:17]=3)[N:12]([CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 21192549HCID 21192549, compound

Product 1

HCID 16073902HCID 16073902, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of N-(4-chlorobenzyl)-6-(chloromethyl)-1-[2-(2-methoxyethoxy)ethyl]-4-oxo-1,4-dihydro-3-quinolinecarboxamide (175 mg) prepared as described in Example No. 84, in DMF (1.5 11) is added sodium thiomethoxide (40 mg). The mixture is stirred for 18 h, then added to 25 ml of rapidly stirred water. The solid is filtered, washed well with water, dried in vacuo, and recrystallized from acetonitrile to afford 139 mg of the title compound as pale yellow crystals.

Workup

  1. customprepared
  2. filtrationThe solid is filtered
  3. washwashed well with water
  4. customdried in vacuo
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-ed2c4206d56f4550a44ba3c1a8fdea2f
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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