2-Chlorobenzothiazole → HCID 69212985, compound

HRID 2054700Notes

Reaction equation

HRID 2054700 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C@H:11]12[CH2:17][C@H:14]([NH:15][CH2:16]1)[CH2:13][N:12]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[OH-].[Na+]>O1CCOCC1>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:15]1[CH2:16][C@@H:11]2[CH2:17][C@H:14]1[CH2:13][N:12]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 14798Sodium HydroxideHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 69212985HCID 69212985, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chlorobenzothiazole (2.57 g; 15.1 mmol) tert-butyl(1S,4S)-(−)-2,5-diazabicyclo-[2.2.1]heptane-2-carboxylate (2.0 g; 10.1 mmol) and dioxane (10 ml) was stirred at reflux for 19 days. Aqueous sodium hydroxide (50 ml; 1 M) was added. The mixture was extracted with ethyl acetate (2×50 ml). Chromatography on silica gel with a mixture of ethyl acetate and petroleum (1:3), gave the title compound as free base (oil). Yield 1.7 g (57%).

Workup

  1. temperatureat reflux for 19 days
  2. extractionThe mixture was extracted with ethyl acetate (2×50 ml)
  3. additionChromatography on silica gel with a mixture of ethyl acetate and petroleum (1:3)

Sources & evidence

ORD record
ord-feacc0a2831a4fe9a4b38bd6e516032a
Source dataset
uspto-grants-2008_02
Patent number
US07329754B2

Reaction notes

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