Sodium Hydroxide → 4-{5-[4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenoxy]-Pentoxy}-Benzonitrile

HRID 732247

Reaction equation

HRID 732247 reaction equation
[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:3])[CH3:2].[OH-].[Na+].Cl[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.ICCCCCOC1C=CC(C#N)=CC=1>C(OC(=O)C)C.CN(C)C=O>[CH:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]#[N:31])=[CH:32][CH:33]=2)=[CH:14][CH:15]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 162024444-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-PhenolHCID 16202445Benzonitrile, 4-[(5-iodopentyl)oxy]-HCID 193815104-((5-Chloropentyl)oxy)benzonitrile

Product 1

HCID 162024464-{5-[4-(5-Isopropyl-2-Methyl-1,3-Thiazol-4-Yl)-Phenoxy]-Pentoxy}-BenzonitrileYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

While 72.6 g of 4-(5-isopropyl-2-methyl-1,3-thiazol-4-yl)-phenol (6) prepared in Example 4 were added to 850 ml of dimethylformamide and stirred, 15.0 g of sodium hydroxide were added. The reaction temperature was gradually increased and stirring was continued at 50-55° C. for 30 min. Thereafter, 70.0 g of 4-(5-chloro-pentoxy)-benzonitrile (8), prepared in Example 5, or 95.3 g of 4-(5-iodo-pentoxy)-benzonitrile (9), prepared in Example 6, were added. The reaction temperature was gradually increased and stirring was continued at 80-90° C. for 3 hr. After the reaction was completed, the temperature was decreased to room temperature, and the resultant reaction mixture was added with 850 ml of ethylacetate, and then washed with water and brine. Subsequently, the ethylacetate layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residual solution was crystallized with ethylacetate and n-hexane, thus obtaining 114 g (yield: 90%) of a title compound as a light yellow solid through the reaction with the compound (8), or 119.6 g (yield: 94%) of a title compound as a light yellow solid through the reaction with the compound (9).

Workup

  1. temperatureThe reaction temperature was gradually increased
  2. stirringstirring
  3. customprepared in Example 6
  4. additionwere added
  5. temperatureThe reaction temperature was gradually increased
  6. stirringstirring
  7. waitwas continued at 80-90° C. for 3 hr
  8. customwas decreased to room temperature
  9. customthe resultant reaction mixture
  10. washwashed with water and brine
  11. dry with materialSubsequently, the ethylacetate layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residual solution was crystallized with ethylacetate and n-hexane

Sources & evidence

ORD record
ord-585ce5ddb7e24ebd94f2f057f89bae11
Source dataset
uspto-grants-2009_09
Patent number
US07585979B2

Linked notes

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