N-bromobutanimide → HCID 59807130, compound

HRID 1922425Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]2=3)[CH2:4][CH2:3]1.C1C(=O)N([Br:26])C(=O)C1>CN(C=O)C.O>[Br:26][C:16]1[CH:17]=[CH:18][C:9]2[N:8]([CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of compound 3 (0.73 g, 2.99 mmol) in DMF (5 mL) was treated with a solution of NBS (0.53 g, 2.99 mmol) in DMF (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours and stored at 0° C. overnight. The reaction mixture was diluted with H2O (100 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (25 mL), dried (Na2SO4) and concentrated. The product was filtered through a short plug of silica gel (2.0 N NH3 in MeOH:CH2Cl2, 2.5:97.5) to give compound 4 (0.915 g, 95.3%) as a yellow oil. 1H-NMR (DMSO-d6) δ 1.56 (m, 4H), 1.72 (m, 4H), 1.96 (td, 2H, J=10.9, 2.2 Hz), 2.15 (s, 3H), 2.65 (m, 2H), 2.76 (m, 2H), 2.93 (m, 2H), 3.14 (m, 1H), 6.83 (d, 1H, J=8.5 Hz), 7.19 (td, 2H, J=8.6, 2.4 Hz); EI-MS (m/z, %) 324 (M+, 14) 322 (M+, 14), 98 (25), 97 (100), 96 (25), 71 (38).

Workup

waitstored at 0° C. overnight
extractionextracted with ethyl acetate (3×25 mL)
washThe combined organic layers were washed with brine (25 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
filtrationThe product was filtered through a short plug of silica gel (2.0 N NH3 in MeOH:CH2Cl2, 2.5:97.5)

Sources & evidence

ORD record: ord-6adcc1514d2241a2805757ff5286d931
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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