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

HRID 2427237Notes

Reaction equation

HRID 2427237 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To the solution of 4-amino-2,6-dichloro phenol (6 g, 26.5 mmol) and 2,6-dichlorobenzothiazole (363) (6 g, 29.4 mmol, 1.1 eq) in DMSO (25 ml), was added K2CO3 (11 g, 80 mmol, 3.0 eq). The mixture was stirred and heated to 160 degree. After 5.5-hr 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 (364) as a black solid (4.52 g, 49%).

Workup

  1. temperatureheated to 160 degree
  2. extractionwas extracted with AcOEt three times
  3. washAnd the organic layer was washed with Brine
  4. dry with materialwas dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customCrude residue was purified by column chromatography (CHCl3/Acetone=9/1, 180 g of silica gel)

Sources & evidence

ORD record
ord-f82f421f294646a59ff6b1605646696b
Source dataset
uspto-grants-2011_06
Patent number
US07968567B2

Reaction notes

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