Acetic Acid → HCID 86594591, compound

HRID 902828Notes

Reaction equation

HRID 902828 reaction equation
C(O)(=O)C.[CH2:5]([O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[S-:23][C:24]#[N:25].[K+].BrBr>O>[NH2:25][C:24]1[S:23][C:21]2[CH:22]=[C:16]([O:15][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH:17]=[CH:18][C:19]=2[N:20]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24408BromineHCID 38359Aniline, p-(decyloxy)-HCID 516872Potassium thiocyanate

Product 1

HCID 86594591HCID 86594591, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, acetic acid (100 ml) was added to the 4-decyloxyaniline 3 (23.4 g, 93.7 mmol) thus obtained, and potassium thiocyanate (23.5 g, 242 mmol) was then added thereto. The solution was thoroughly cooled in an ice bath, and an acetic acid solution of bromine (5.8 ml/50 ml) was then added dropwise thereto over a period of about 3 hr. After the completion of the dropwise addition of the solution, the mixture was stirred at room temperature for about 2 hr. Thereafter, water (200 ml) was added, and the mixture was refluxed for about 30 min and was then hot-filtered. The filtrate was made alkaline by the addition of aqueous ammonia, and saturated brine was further added thereto. The precipitated solid was collected by filtration to give 2-amino-6-decyloxybenzothiazole 4 (14.22 g, 49.5%) as a light purple solid. The product was purified by column chromatography on silica gel (hexane: AcOEt=1:2).

Workup

  1. customthus obtained
  2. temperatureThe solution was thoroughly cooled in an ice bath
  3. additionAfter the completion of the dropwise addition of the solution
  4. temperaturethe mixture was refluxed for about 30 min
  5. filtrationwas then hot-filtered
  6. additionby the addition of aqueous ammonia, and saturated brine
  7. additionwas further added
  8. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-4304712af7ce469b8b2f89538b7ed630
Source dataset
uspto-grants-2008_04
Patent number
US07365359B2

Reaction notes

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