Hydrochloric Acid → 3,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine

HRID 1370495

反応式

HRID 1370495 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.Cl[C:12]1[S:13][C:14]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:15]=2[N:16]=1.C([O-])([O-])=O.[K+].[K+].Cl>CS(C)=O.O>[Cl:8][C:6]1[CH:7]=[C:2]([NH2:1])[CH:3]=[C:4]([Cl:10])[C:5]=1[O:9][C:12]1[S:13][C:14]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:15]=2[N:16]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 771762,6-DichlorobenzothiazoleHCID 800374-Amino-2,6-dichlorophenol

生成物 1

HCID 221487763,5-Dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine収率 49.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

To the solution of 4-amino-2,6-dichloro phenol (6 g, 26.5 mmol) and 2,6-dichlorobenzothiazole (101) (6 g, 29.4 mmol, 1.1 equiv.) in DMSO (25 mL), was added K2CO3 (11 g, 80 mmol, 3.0 equiv.). The mixture was stirred and heated to 160° C. After 5.5 h water (20 mL) was added to the reaction mixture, which was neutralized with 2N HCl., and was extracted with AcOEt three times. And the organic layer was washed with brine and was dried over anhydrous MgSO4, and then concentrated. Crude residue was purified by column chromatography (CHCl3/acetone=9/1, 180 g of silica gel) to afford 3,5-dichloro-4-(6-chloro-benzothiazol-2-yloxy)-phenylamine (102) as a black solid (4.52 g, 49%).

後処理

  1. extraction, and was extracted with AcOEt three times
  2. washAnd the organic layer was washed with brine
  3. dry with materialwas dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customCrude residue was purified by column chromatography (CHCl3/acetone=9/1, 180 g of silica gel)

出典と根拠

ORDレコード
ord-bf033d1d5294458c906b11d1d1b50641
出典データセット
uspto-grants-2003_06
特許番号
US06583157B2

関連ノート

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