Bromine → 5-Bromo-1,3-benzothiazol-2-amine

HRID 2378559Notes

Reaction equation

HRID 2378559 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[CH:6][CH:7]=1.BrBr>C(Cl)(Cl)Cl>[NH2:11][C:9]1[S:10][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[N:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27356191-(3-bromophenyl)thiourea

Product 1

HCID 137757855-Bromo-1,3-benzothiazol-2-amineYield 47.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of Intermediate 74 (1.29 g) in chloroform (12 ml) was added dropwise with a solution of bromine (272 μl, WAKO) in chloroform (1.5 ml), refluxed by heating for 2.5 hours, and stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, neutralized with 5% aqueous ammonia, and then added with water (50 ml) and methylene chloride (150 ml) for extraction. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 75, 609 mg).

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 2.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionadded with water (50 ml) and methylene chloride (150 ml) for extraction
  5. customThe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-80846b5db6684b528ad62e2bf20204d4
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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