Boron tribromide → 2-[4-(Methylamino)phenyl]-1,3-benzothiazol-6-ol

HRID 2276907Notes

Reaction equation

HRID 2276907 reaction equation
B(Br)(Br)Br.[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][CH:8]=1>ClCCl>[CH3:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][C:15]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9835167HCID 9835167, compound

Product 1

HCID 101714872-[4-(Methylamino)phenyl]-1,3-benzothiazol-6-olYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding BBr3 (1.0 M in CH2Cl2, 10.5 mL, 10.5 mmol) to 2-[4-(N-monomethyl)aminophenyl]-6-methoxybenzothiazole (44, 588 mg, 2.06 mmol) obtained in step 3 dissolved in dichloromethane (25 mL), the mixture was agitated for 12 hours at room temperature. After cautiously adding water and sodium bicarbonate aqueous solution, the organic compound was extracted using dichloromethane. Then, after removing water using sodium sulfate, 2-[4-(N-monomethyl)aminophenyl]-6-hydroxybenzothiazole (45, 530 mg, 99%) was yielded as a yellow solid without further purification.

Workup

  1. customobtained in step 3
  2. extractionAfter cautiously adding water and sodium bicarbonate aqueous solution, the organic compound was extracted
  3. customThen, after removing water

Sources & evidence

ORD record
ord-9f97aa21a54e47feaa46da60403cf2e3
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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