Bromine → N-(6-Bromo-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide

HRID 1807675Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[N:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[Br:15]Br>CC(O)=O>[Br:15][CH:3]1[CH2:4][CH2:5][C:6]2[N:7]=[C:8]([NH:11][C:12](=[O:14])[CH3:13])[S:9][C:10]=2[C:2]1=[O:1]

Participants

Conditions

Temperature: 75 °C

Procedure

N-(7-Oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide (Stage T.4, 2.286 g, 10.87 mmol) was dissolved in AcOH (60 ml), then bromine (1.74 g, 10.87 mmol) dissolved in AcOH (10 mL) were slowly added and the RM was heated to 75° C. for 20 h. The color changed from red to beige. The mixture was evaporated and the residue was dissolved in MeOH (10 mL) and precipitated with H2O. The mixture was filtered and dried on HV. The crude material was chromatographed with MPLC C18 H2O 0.1% TFA/CH3CN 0.1% TFA, gradient 0-50%. Fractions containing the product were neutralized with NaHCO3, extracted with EtOAc and lyophilized from dioxane to give of the title compound as a white solid (M+H=291; M−H=289; tR 4.29 (Method F)). 1H-NMR (d6-DMSO, 600.13 MHz) 12.75 (s, 1H) 4.95 (t, 1H), 2.95-2.84 (m, 2H), 2.62-2.52 (m, 1H), 2.40-2.30 (m, 1H), 2.20 (s, 3H).

Workup

additionwere slowly added
customThe mixture was evaporated
dissolutionthe residue was dissolved in MeOH (10 mL)
customprecipitated with H2O
filtrationThe mixture was filtered
customdried on HV
customThe crude material was chromatographed with MPLC
additionFractions containing the product
extractionextracted with EtOAc

Sources & evidence

ORD record: ord-ef87bc10edec48bcb8d8edc86904b3ca
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08357707B2

Reaction notes

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