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

HRID 732247

反応式

HRID 732247 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-585ce5ddb7e24ebd94f2f057f89bae11
出典データセット
uspto-grants-2009_09
特許番号
US07585979B2

関連ノート

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