Water → HCID 10633484, compound

HRID 257294Notes

Reaction equation

HRID 257294 reaction equation
[CH2:1]([C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[S-:14][C:15]#[N:16].[K+].BrBr.O>C(O)(=O)C>[NH2:16][C:15]1[S:14][C:12]2[CH:13]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=[CH:9][C:10]=2[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 363824-HexylanilineHCID 516872Potassium thiocyanate

Product 1

HCID 10633484HCID 10633484, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

In a 2 liter-reaction vessel, 50.0 g (0.28M) of p-hexylaniline, 54.8 g (0.56M) of potassium thiocyanate and 400 ml of acetic acid were placed and cooled below 10° C. To the mixture, a solution of 45.0 g of bromine in 135 ml of acetic acid was added dropwise in 40 minutes below 10° C. under strong stirring, followed by reaction for 1.5 hours below 10° C. After the reaction, 500 ml of water was poured into the reaction mixture, followed by heating to dissolve the resultant precipitate. The resultant solution was filtered under heating. Ammonia water was added to the filtrate until the resultant solution became basic, followed by cooling with ice to precipitate a crystal. The crystal was recovered by filtration, followed by washing and drying to obtain a crude product. The crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1) to obtain 33.0 g of 2-amino-6-hexylbenzothiazole (Yield: 49.9 %).

Workup

  1. temperaturecooled below 10° C
  2. customfollowed by reaction for 1.5 hours below 10° C
  3. additionwas poured into the reaction mixture
  4. temperatureby heating
  5. filtrationThe resultant solution was filtered
  6. temperatureunder heating
  7. additionAmmonia water was added to the filtrate until the resultant solution
  8. temperatureby cooling with ice
  9. customto precipitate a crystal
  10. filtrationThe crystal was recovered by filtration
  11. washby washing
  12. customdrying
  13. customto obtain a crude product
  14. customThe crude product was recrystallized from a mixture solvent of n-hexane/benzene (1/1)

Sources & evidence

ORD record
ord-6b9f2fcee88d4e1ba4fbb7f1d17b4c32
Source dataset
uspto-grants-1993_11
Patent number
US05262083

Reaction notes

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