Ammonia → 2-Amino-5,7-dibromobenzothiazole

HRID 1941926Notes

Reaction equation

HRID 1941926 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[C:6]([Br:8])[CH:7]=1.BrBr.N>C(Cl)(Cl)Cl.O>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[C:5]2[S:11][C:10]([NH2:12])=[N:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 20157487HCID 20157487, compound

Product 1

HCID 578136892-Amino-5,7-dibromobenzothiazoleYield 100.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of (3,5-dibromo-phenyl)-thiourea (35 g, 0.11 mol) in CHCl3 (600 mL) at −55-60° C. was added dropwise a solution of Br2 (40.40 g, 0.25 mol, in 100 ml of CHCl3) over a period of 1 h. The reaction mixture was stirred at −55-60° C. for 15 min followed by refluxing at 70-75° C. for 3 h. The reaction mixture was cooled to room temperature and filtered to get the crude residue that was washed with hexane and diethyl ether. The solid thus obtained was dissolved in H2O, basified with aqueous ammonia solution to pH 10-12 and stirred for 30 min. The solid thus obtained was filtered and washed with water to get the desired product (34.0 g, 98%).

Workup

  1. temperatureby refluxing at 70-75° C. for 3 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered
  4. customto get the crude residue that
  5. washwas washed with hexane and diethyl ether
  6. customThe solid thus obtained
  7. stirringstirred for 30 min
  8. customThe solid thus obtained
  9. filtrationwas filtered
  10. washwashed with water

Sources & evidence

ORD record
ord-c5cdd9ecf68c4e73a0f10f7fbf337197
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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