Potassium Bromide → 2-Bromo-6-octylbenzo[d]thiazole

HRID 1802119Notes

Reaction equation

HRID 1802119 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.O.[CH2:13]([C:21]1[CH:30]=[CH:29][C:24]2[N:25]=[C:26](N)[S:27][C:23]=2[CH:22]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].N([O-])=O.[Na+].[K+].[Br-:36]>CC#N.O>[Br:36][C:26]1[S:27][C:23]2[CH:22]=[C:21]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:30]=[CH:29][C:24]=2[N:25]=1

Participants

7

Reactant 4

HCID 253877Potassium BromideHCID 521998p-Toluenesulfonic acid monohydrateHCID 138146496-Octylbenzo[d]thiazol-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 674100392-Bromo-6-octylbenzo[d]thiazoleYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
12.5 °C

Procedure

To a solution of p-TsOH.H2O (108 mg, 0.57 mmol) in MeCN (2 mL) was added compound 6-octylbenzo[d]thiazol-2-amine (50 mg, 0.19 mmol). The resulting suspension was cooled to 10-15° C. and to this was added, gradually, a solution of NaNO2 (26 mg, 0.38 mmol) and KBr (56 mg, 0.48 mmol) in H2O (0.5 mL). The mixture was then stirred at r.t. for 1 h. Then the mixture was extracted with EtOAc and purified by silica gel chromatography using PE to give product the title compound (50 mg, 82%). 1H NMR (300 MHz, CDCl3) δ7.880 (t, 1H), 7.585 (s, 1H), 7.286 (t, 1H), 2.711 (t, 2H), 1.686-1.571 (m, 2H), 1.309-1.186 (m, 10H), 0.874 (t, 3H).

Workup

  1. additionto this was added
  2. extractionThen the mixture was extracted with EtOAc
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-74499fbb75584f4dba9d5af9abeca3a0
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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