Potassium Carbonate → 3,5-Dichloro-4-(4-chloro-benzothiazol-2-yloxy)-phenylamine

HRID 1819803Notes

Reaction equation

HRID 1819803 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[C:17]([Cl:19])[C:16]([OH:20])=[C:15]([Cl:21])[CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O>[Cl:19][C:17]1[CH:18]=[C:13]([NH2:12])[CH:14]=[C:15]([Cl:21])[C:16]=1[O:20][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 771772,4-DichlorobenzothiazoleHCID 800374-Amino-2,6-dichlorophenol

Product 1

HCID 185115923,5-Dichloro-4-(4-chloro-benzothiazol-2-yloxy)-phenylamineYield 33.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

To solution of 2,4-dichlorobenzothiazole (255, 2.23 g, 11 mmol) and 4-amino-2,6-dichlorophenol (Aldrich, 1.78 g, 10 mmol) in 10 mL of DMSO was add K2CO3 (Aldrich, 4.14 g, 30 mmol). The mixture was heated at 145° C. for 4 h. After cooled to room temperature, the reaction mixture was diluted with EtOAc (300 mL) and filtered through a pad of silica gel and activated carbon followed by washing with EtOAc (500 mL). The filtrate was concentrated and the residue was purified by chromatography (20%-30% EtOAc/Hexanes) to give 1.15 g (33%) of product. 1H NMR (400 MHz, DMSO-d6) δ 7.92 (d, J=8.0 Hz, 1H), 7.55 (d, J=7.9 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), 6.75 (s, 2H), 5.93 (s, 2H). MS (EI): m/z 345 (M+H).

Workup

  1. temperatureAfter cooled to room temperature
  2. filtrationfiltered through a pad of silica gel and activated carbon
  3. washby washing with EtOAc (500 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by chromatography (20%-30% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c8b033a2c93545d58d6162e546b7ed24
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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