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

HRID 709902Notes

Reaction equation

HRID 709902 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].[C:16]([S-:18])#[N:17].[K+].BrBr.O>CC(O)=O>[CH2:1]([C:9]1[CH:10]=[CH:11][C:12]2[N:13]=[C:16]([NH2:17])[S:18][C:14]=2[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 853464-OctylanilineHCID 516872Potassium thiocyanate

Product 1

HCID 138146496-Octylbenzo[d]thiazol-2-amineYield 70.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

4-octylaniline (500 mg, 2.5 mmol), AcOH (4 mL), and KSCN (970 mg, 10 mmol) were stirred at r.t. for 10 min, and then a solution of bromine (0.13 mL, 2.5 mmol) in AcOH (2 mL) was added to the mixture over 20 min. The reaction mixture was stirred at r.t. for 8 h, then poured into cold water and extracted with EtOAc. The organic layer was purified by silica gel chromatography using PE/EA (3/1) to give compound the title compound (460 mg, 70%). 1H NMR (300 MHz, CDCl3) δ 7.446 (s, 1H), 7.320 (s, 1H), 7.230 (d, 1H), 2.577 (t, 2H), 1.567-1.506 (m, 2H), 1.266-1.167 (m, 10H), 0.847 (t, 3H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ba263fc9df3f49d3ba2d5e3cd136a7e8
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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