N-bromobutanimide → HCID 68617641, compound

HRID 1887256Notes

Reaction equation

[CH2:1]([NH:3][C:4]([C:6]1[S:7][CH:8]=[CH:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[Br:12]N1C(=O)CCC1=O>>[Br:12][C:8]1[S:7][C:6]([C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[C:10]([CH3:11])[CH:9]=1

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 16639189HCID 16639189, compound

Product 1

HCID 68617641HCID 68617641, compoundYield 92%

Procedure

Following the procedure as described in Preparation 19, making variations only as required to use N-ethyl-3-methylthiophene-2-carboxamide in place of N-benzyl-3-methylfuran-2-carboxamide to react with N-bromosuccinimide, 5-bromo-N-ethyl-3-methylthiophene-2-carboxamide was obtained as a colorless oil in 92% yield: 1H NMR (300 MHz, CDCl3) δ 6.85 (s, 1H), 5.65 (br s, 1H), 3.48-3.38 (m, 2H), 2.45 (s, 3H), 1.22 (t, J=7.3 Hz, 3H); MS (ES+) m/z 248.1 (M+1), 250.1 (M+1).

Workup

customas described in Preparation 19

Sources & evidence

ORD record: ord-ed9b0717b146458c92338731056e2e99
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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