Chloroform → 2-Benzothiazolamine, 4-chloro-

HRID 408113

Reaction equation

HRID 408113 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrBr.C(Cl)(Cl)[Cl:14]>>[Cl:14][C:6]1[C:1]2[N:7]=[C:8]([NH2:10])[S:9][C:2]=2[CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 6212Chloroform2×HCID 24408BromineHCID 676454Phenylthiourea

Product 1

HCID 298722-Benzothiazolamine, 4-chloro-

Conditions

Temperature
0 °C

Procedure

The phenylthiourea (6.00 g, 32.16 mmol) was dissolved in CHCl3 (150 mL) and cooled to 0° C. with an ice bath. To this mixture was added a solution of Br2 (1.6 mL, 32.2 mmol) in CHCl3 (100 mL) dropwise over 30 min. After the addition, the mixture was stirred at 0° C. for 1 h, then allowed to warm to rt. the reaction was refluxed for 3 h to 4 h than allowed to cool to room temperature. The organic solvent was removed and the residue was washed with sulfurous acid. The residue was then neutralized with liquid ammonia. The solid was filtered off, washed with watyer and recrystallized from EtOH.

Workup

  1. additionAfter the addition
  2. temperatureto warm to rt
  3. temperaturethe reaction was refluxed for 3 h to 4 h
  4. temperatureto cool to room temperature
  5. customThe organic solvent was removed
  6. washthe residue was washed with sulfurous acid
  7. filtrationThe solid was filtered off
  8. washwashed with watyer
  9. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-14f9242d6ba64935a248220f71c35a5b
Source dataset
uspto-grants-2014_06
Patent number
US08759336B2

Linked notes

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