Azobisisobutyronitrile → 4-Bromomethyl-2-bis(tert-butoxycarbonyl)aminobenzothiazole

HRID 2274635Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:12]=2[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:26]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:18][C:14]1[C:12]2[N:13]=[C:9]([N:8]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[S:10][C:11]=2[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(bis(tert-butoxycarbonyl)amino)-4-methylbenzothiazole (1.09 g, 3.00 mmol) in carbon tetrachloride (15 ml) were added N-bromosuccinimide (694 mg, 3.90 mmol) and 2,2′-azobis(isobutyronitrile) (99 mg, 0.20 mmol) and the mixture was stirred under nitrogen atmosphere at 80° C. for 2 hr. The reaction mixture was allowed to cool to room temperature and concentrated in vacuo. The crude residue was subjected to column chromatography (eluent: n-hexane:chloroform=60:40 to 50:50) to obtain the title compound (1.26 g, 95%).

Workup

temperatureto cool to room temperature
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-95e181714903428ba1e31d62b252c622
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126981B2

Reaction notes

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