Sodium Hydroxide → HCID 19378832, compound

HRID 327144Notes

Reaction equation

HRID 327144 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]SC1SCC(=O)N=1.[CH2:24]([C:26]1[NH:27][CH:28]=[CH:29][N:30]=1)[CH3:25].[OH-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:27]1[CH:28]=[CH:29][N:30]=[C:26]1[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 661302-EthylimidazoleHCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-one

Product 1

HCID 19378832HCID 19378832, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir at room temperature for four days 2 gms. of the iodide prepared in Examples 2 or 3, 2 gms. of 2-ethylimidazole, 2.5 ml. DMF and 0.4 gm sodium hydroxide in a reaction flask. Remove the solvent and partition with water/methylene chloride. Elute on a silica column with 100% methylene chloride and then lot methanol to yield the title compound. MS:m/z 337 (M+) H1 -NMR-200 mHz, δH (CDCl3), 1.34 (3H,t,J 7.5 Hz), 1.3-1.65 (4H,m), 1.70-1.90 (4H,m) 2.66 (2H,q,J 7.5 Hz), 3.75 (3H,s), 3.83 (2H,t,J 7 Hz), 3.95 (2H,t,J 6 Hz), 6.7-7.0 (5H,M).

Workup

  1. customRemove the solvent
  2. custompartition with water/methylene chloride
  3. washElute on a silica column with 100% methylene chloride

Sources & evidence

ORD record
ord-da74e66927f64c7a8df6070a3a9d1268
Source dataset
uspto-grants-1993_12
Patent number
US05272167

Reaction notes

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