Methanol → HCID 59823517、化合物

HRID 1426865ノート

反応式

HRID 1426865 の反応式
[H-].[Na+].[NH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1.Cl[C:14]1[S:15][C:16]([Cl:20])=[C:17]([Cl:19])[N:18]=1.CO>CN(C)C=O.C(OCC)(=O)C.O>[Cl:19][C:17]1[N:18]=[C:14]([O:11][C:7]2[C:6]([CH3:12])=[CH:5][C:4]([NH2:3])=[C:9]([CH3:10])[CH:8]=2)[S:15][C:16]=1[Cl:20]

参加物

8

反応物 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 765444-Amino-2,5-dimethylphenolHCID 3016564Trichlorothiazole

生成物 1

HCID 59823517HCID 59823517、化合物収率 55.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

1.3 g (33 mmol) sodium hydride (60% in oil) were added portionwise to a solution of 4.1 g (30.0 mmol) of 4-amino-2,5-dimethylphenol in 30 ml of dimethylformamide. After the gas evolution has stopped, 5.6 g (30 mmol) of 2,4,5-trichloro-1,3-thiazole were added and the reaction mixture was stirred for 1 h at 100° C. At ambient temperature 0.5 ml methanol, 10 ml of water and 100 ml of ethyl acetate were added successively. The organic layer was separated, the watery layer extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate. Concentration in vacuo and column chromatographie (petroleum ether/acetone 4/1) yielded 4.8 g (16.6 mmol, 55%) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline log P (pH=2.3)=3.4

後処理

  1. customThe organic layer was separated
  2. extractionthe watery layer extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationConcentration in vacuo and column chromatographie (petroleum ether/acetone 4/1)

出典と根拠

ORDレコード
ord-cc9423bda7674ec0b551325e47a5ddde
出典データセット
uspto-grants-2015_01
特許番号
US08933107B2

反応ノート

読み込み中…