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

HRID 1370495

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HRID 1370495 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
160 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-bf033d1d5294458c906b11d1d1b50641
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583157B2

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