Ammonium thiocyanate → 2-Amino-6-benzylbenzothiazole

HRID 359779Notes

Reaction equation

HRID 359779 reaction equation
BrBr.[CH2:3]([C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[S-:17][C:18]#[N:19].[NH4+]>C(O)(=O)C>[NH2:19][C:18]1[S:17][C:15]2[CH:16]=[C:10]([CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:11]=[CH:12][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 24408BromineHCID 136914Benzenamine, 4-(phenylmethyl)-

Product 1

HCID 219855102-Amino-6-benzylbenzothiazoleYield 72.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

11.2 ml of bromine were added dropWise to a solution of 39.7 g of 4-benzylaniline and 33 g of ammonium thiocyanate in 400 ml of acetic acid at a temperature of from 12 to 18° C. After completion of the addition, the mixture was stirred at room temperature for 2 hours and then the solvent was distilled off. The residue was mixed with 600 ml of ethyl acetate and 300 ml of water and the mixture was neutralized by the addition of potassium carbonate powder The ethyl acetate layer was separated, washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residual solid was recrystallized from ethyl acetate to give 37.6 g of the title compound melting at 173-175° C.

Workup

  1. additionAfter completion of the addition
  2. distillationthe solvent was distilled off
  3. additionThe residue was mixed with 600 ml of ethyl acetate and 300 ml of water
  4. additionthe mixture was neutralized by the addition of potassium carbonate powder The ethyl acetate layer
  5. customwas separated
  6. washwashed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe residual solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4b952dbd65624c0991f333c02a6b3d20
Source dataset
uspto-grants-1991_03
Patent number
US05002942

Reaction notes

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