N-bromobutanimide → HCID 67389127, compound

HRID 1926335Notes

Reaction equation

HRID 1926335 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][CH:15]=1.C1C(=O)N([Br:24])C(=O)C1>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[C:14]([Br:24])[CH:15]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimide2×HCID 675209593-Benzothiazol-2-ylpyridin-2-ylamine

Product 1

HCID 67389127HCID 67389127, compound

Procedure

The title compound was prepared from 3-benzothiazol-2-ylpyridin-2-ylamine (22.7 g, 100 mmol) and NBS (17.8 g, 100 mmol) as a brown solid following the General Procedure for the Bromination of Aminopyridines with NBS. 1H NMR (CDCl3, 300 MHz): δ=7.17 (brs, 2H), 7.41 (t, J=6.9 Hz, 1H), 7.50 (t, J=6.9 Hz, 1H), 7.89 (d, J=2.4 Hz, 1H), 7.95 (d, J=2.4 Hz, 1H), 8.03 (d, J=2.1 Hz, 1H), 8.20 (d, J=2.1 Hz, 1H). MS(ES+): m/z=305.98/307.94 (91/100) [MH+]. HPLC: tR=3.62 min (nonpolar—5 min, ZQ3).

Workup

  1. customHPLC: tR=3.62 min (nonpolar—5 min, ZQ3)

Sources & evidence

ORD record
ord-d8650bb7f3fe4e819cb02b40f52974f6
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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