Pyridine → 7-(Bromomethyl)-N-mesityl-1,3-benzothiazol-2-amine

HRID 2235524Notes

Reaction equation

HRID 2235524 reaction equation
O[CH2:2][C:3]1[C:11]2[S:10][C:9]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.P(Br)(Br)[Br:29]>ClCCl>[Br:29][CH2:2][C:3]1[C:11]2[S:10][C:9]([NH:12][C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 860491207-(Hydroxymethyl)-N-mesityl-1,3-benzothiazol-2-amine

Product 1

HCID 860491237-(Bromomethyl)-N-mesityl-1,3-benzothiazol-2-amineYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.065 g (0.22 mmol) of 7-(hydroxymethyl)-N-mesityl-1,3-benzothiazol-2-amine in 2 mL of dichloromethane was added 58 μL (0.72 mmol) of pyridine and 0.24 mL (0.24 mmol) of phosphorous tribromide (1 M in dichloromethane). The reaction was stirred at room temperature for 8 h and quenched with saturated sodium bicarbonate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give 0.045 g (57%) of the title compound that was used without further purification.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-701e9c8cd1ae49199b3bdad018753b62
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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