Iodine → 3-(3-Iodo-l,l-dimethyl-2-propynyloxymethyloxy)-4-cyano-5-methylthioisothiazole

HRID 1901551ノート

反応式

HRID 1901551 の反応式
[OH:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH3:10])[S:4][N:3]=1.[CH3:11][C:12](Cl)([O:14][CH2:15][C:16]#[CH:17])[CH3:13].[I:19]I.[I-].[K+].[OH-].[K+]>CN(C=O)C>[I:19][C:17]#[C:16][CH2:15][O:14][C:12]([CH3:13])([CH3:11])[O:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([S:9][CH3:10])[S:4][N:3]=1

参加物

7

反応物 5

HCID 807IodineHCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 867500271,1-Dimethyl-2-propynyloxymethyl chlorideHCID 178503646HCID 178503646、化合物

生成物 1

HCID 233683353-(3-Iodo-l,l-dimethyl-2-propynyloxymethyloxy)-4-cyano-5-methylthioisothiazole収率 60%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

1.7 Grams of 3-hydroxy-4-cyano-5-methylthioisothiazole was dissolved in 30 ml of DMF, 1.4 g of 1,1-dimethyl-2-propynyloxymethyl chloride was added thereto, and then the reaction solution was stirred at 50° C. for 1 hour. Thereafter, the reaction solution was ice-cooled to 5° to 10° C., 5.1 g of iodine and 3.5 g of potassium iodide were added thereto, and then 6.6 g of 10% KOH was added dropwise. The temperature of the reaction solution was returned to room temperature, and after stirring for 1 hour, the reaction solution was extracted with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure to obtain crude crystals. The crystals were recrystallized from ether to obtain 2.4 g of crystals having a melting point of 96° to 97° C. (yield 60%).

後処理

  1. temperaturecooled to 5° to 10° C.
  2. customwas returned to room temperature
  3. stirringafter stirring for 1 hour
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto obtain crude crystals
  9. customThe crystals were recrystallized from ether

出典と根拠

ORDレコード
ord-e40c96a4a7854cac9d0dc14f489e3ecf
出典データセット
uspto-grants-1996_11
特許番号
US05578622

反応ノート

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