tert-Butanol → 945400-88-4

HRID 1698107Notes

Reaction equation

C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[Br:25][C:26]1[S:27][C:28]2C=C(C(O)=O)[CH:32]=[CH:31][C:29]=2[N:30]=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>>[Br:25][C:26]1[S:27][C:28]2[CH:7]=[C:6]([NH:3][C:4](=[O:15])[O:42][C:38]([CH3:41])([CH3:40])[CH3:39])[CH:32]=[CH:31][C:29]=2[N:30]=1

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 457896282-Bromo-1,3-benzothiazole-6-carboxylic acid

Product 1

HCID 57553402945400-88-4

Conditions

Temperature: 80 °C

Procedure

Triethylamine (1.94 mL, 13.9 mmol) and diphenylphosphoryl azide (2.76 mL, 12.8 mmol) were added to a solution of 2-bromo-1,3-benzothiazole-6-carboxylic acid (3.0 g, 11.6 mmol) in tert-butanol (100 mL) and the reaction mixture was stirred at 80° C. for 4 h. The solvent was evaporated under reduced pressure and the residue was subjected to flash chromatography (Heptane/EtOAc gradient) to give tert-butyl (2-bromo-1,3-benzothiazol-6-yl)carbamate (1.1 g) as a white solid. MS m/z (M+H) 329, 331.

Workup

customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-91c2164b351c4d1885594a1f354f9900
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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