Water → 6-Octylbenzo[d]thiazol-2-amine

HRID 1613530Notes

Reaction equation

HRID 1613530 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[S-:16][C:17]#[N:18].[K+].BrBr.O>C(O)(=O)C>[NH2:18][C:17]1[S:16][C:14]2[CH:15]=[C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:10]=[CH:11][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 853464-OctylanilineHCID 516872Potassium thiocyanate

Product 1

HCID 138146496-Octylbenzo[d]thiazol-2-amineYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In a 2 liters-reaction vessel, 50.0 g (0.24M) of p-octylaniline, 47.3 g (0.49M) of potassium thiocyanate and 350 ml of acetic acid were placed and cooled below 10° C. Under intersive stirring, a solution of 39.0 g of bromine in 120 ml of acetic acid was added dropwise to the above mixture in 75 minutes below 10° C., followed by reaction for 2 hours below 10° C. After the reaction, 500 ml of water was added to the reaction mixture and heated to dissolve the precipitate, followed by filtration under heating. Ammonia water was added to the filtrate so as to provide a basic solution, followed by cooling on an iced bath to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and drying to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate) to obtain 41.2 g of 2-amino-6-octylbenzothiazole (Yield: 68%).

Workup

  1. temperaturecooled below 10° C
  2. customfollowed by reaction for 2 hours below 10° C
  3. additionwas added to the reaction mixture
  4. temperatureheated
  5. dissolutionto dissolve the precipitate
  6. filtrationfollowed by filtration
  7. temperatureunder heating
  8. additionAmmonia water was added to the filtrate so as
  9. customto provide a basic solution
  10. temperatureby cooling on an iced bath
  11. customto precipitate a crystal
  12. filtrationThe crystal was recovered by filtration
  13. washby washing with water
  14. customdrying
  15. customto obtain a crude product
  16. customThe crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6270a12f6959459e882575a27beebcfa
Source dataset
uspto-grants-1993_03
Patent number
US05194177

Reaction notes

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