Water → 6-Amino-7-bromobenzothiazole

HRID 389478Notes

Reaction equation

HRID 389478 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH2:10])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:11]Br.O>C(O)(=O)C>[Br:11][C:6]1[C:5]2[S:1][CH:2]=[N:3][C:4]=2[CH:9]=[CH:8][C:7]=1[NH2:10]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 682886-Aminobenzothiazole

Product 1

HCID 47126206-Amino-7-bromobenzothiazoleYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of benzothiazol-6-ylamine (6.4 g, 42.6 mmol) in glacial acetic acid (40 mL) was added bromine (2.18 mL) in glacial acetic acid (10 mL) dropwise. The reaction mixture was stirred at RT for 1 h. Water (160 mL) was added to the reaction mixture and the solid formed was extracted with ethyl acetate (3×40 mL). The combined organic fractions were washed with saturated aqueous sodium bicarbonate solution (200 mL), water (100 mL), and brine (20 mL), dried over anhydrous sodium sulfate, and concentrated. Purification of the residue by column chromatography (20% ethyl acetate:hexanes) afforded 6.5 g (67%) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 4.31 (br. s, 2H), 7.02 (d, J=8.4 Hz, 1H), 7.92 (d, J=8.4 Hz, 1H), 8.80 (s, 1H).

Workup

  1. customthe solid formed
  2. extractionwas extracted with ethyl acetate (3×40 mL)
  3. washThe combined organic fractions were washed with saturated aqueous sodium bicarbonate solution (200 mL), water (100 mL), and brine (20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the residue by column chromatography (20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f0ea0bde794b42c09a74c7af41f954c5
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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