Bromine → 2-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one

HRID 595079

反応式

HRID 595079 の反応式
[CH3:1][C:2]1([CH3:10])[CH2:7][C:6](=[O:8])[CH2:5][C:4](=O)[CH2:3]1.CC([O-])=O.[Na+].BrBr.[NH2:18][C:19]([NH2:21])=[S:20]>CC(O)=O>[NH2:21][C:19]1[S:20][C:5]2[C:6](=[O:8])[CH2:7][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]=2[N:18]=1

参加物

6

反応物 4

HCID 24408BromineHCID 31358DimedoneHCID 517045Sodium AcetateHCID 2723790Thiourea

生成物 1

HCID 5878742-Amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one収率 75.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

5,5-Dimethyl-cyclohexane-1,3-dione (201 g, 1.43 mol) and NaOAc (176 g, 2.14 mol) are suspended in AcOH (2 L) and Br2 (229 g, 1.43 mol) is added in dropwise while maintaining the reaction temperature between 15 and 20° C. After complete addition, the reaction is stirred at RT overnight. Thiourea (109 g, 1.43 mol) is added in portions and the reaction mixture is heated at 100° C. for 1 h. After cooling to RT, the AcOH is removed in vacuo and the resulting crude product is diluted with water (1 L) and neutralized with an aqueous saturated NaHCO3 solution. The resulting mixture is extracted with ethyl acetate (4×500 mL). The organic layer is washed with brine (500 mL), dried over anhydrous Na2SO4 and the solvent is evaporated in vacuo to give crude product. The crude product is washed with water (1.5 L) to yield 2-amino-5,5-dimethyl-5,6-dihydro-4H-benzothiazol-7-one (211 g, 75% yield).

後処理

  1. temperaturewhile maintaining the reaction temperature between 15 and 20° C
  2. additionAfter complete addition
  3. temperaturethe reaction mixture is heated at 100° C. for 1 h
  4. temperatureAfter cooling to RT
  5. customthe AcOH is removed in vacuo
  6. additionthe resulting crude product is diluted with water (1 L)
  7. extractionThe resulting mixture is extracted with ethyl acetate (4×500 mL)
  8. washThe organic layer is washed with brine (500 mL)
  9. dry with materialdried over anhydrous Na2SO4
  10. customthe solvent is evaporated in vacuo
  11. customto give crude product
  12. washThe crude product is washed with water (1.5 L)

出典と根拠

ORDレコード
ord-d4cdbd65aaa3462697dbdaa6824b1482
出典データセット
uspto-grants-2016_01
特許番号
US09243000B2

関連ノート

読み込み中…