Potassium Carbonate → 7-Nitro-1,3-benzothiazol-2-amine

HRID 2235498Notes

Reaction equation

HRID 2235498 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]([NH2:13])=[S:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].BrBr.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)(Cl)Cl.O>[N+:1]([C:4]1[C:5]2[S:12][C:11]([NH2:13])=[N:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 2754758(3-Nitrophenyl)thiourea

Product 1

HCID 43257247-Nitro-1,3-benzothiazol-2-amineYield 51.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To 0.60 g (3.0 mmol) of (3-nitrophenyl)thiourea in 25 mL of carbon tetrachloride was added 0.17 mL (3.4 mmol) of bromine in 10 mL of carbon tetrachloride dropwise over 1 h. The mixture was heated to reflux for 18 h, cooled to room temperature and the precipitate that formed was collected by filtration. The precipitate was slurried in glacial acetic acid and the solids were collected by filtration. The solids thus obtained were slurried in water and saturated potassium carbonate was added until the pH was about 9. The free base was collected by filtration to give 0.30 g (51%) of the title compound as a light orange solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. customthe precipitate that formed
  4. filtrationwas collected by filtration
  5. filtrationthe solids were collected by filtration
  6. customThe solids thus obtained
  7. filtrationThe free base was collected by filtration

Sources & evidence

ORD record
ord-50d2f6438b6149d9a13e9cc78b5d1609
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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