N-bromobutanimide → HCID 69188051, compound

HRID 448095Notes

Reaction equation

HRID 448095 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8](=[O:21])/[CH:9]=[C:10]2\[S:11][CH:12]=[C:13]([CH3:20])[N:14]\2[CH2:15][CH:16]2[CH2:19][CH2:18][CH2:17]2)[CH:7]=1.[Br:24]N1C(=O)CCC1=O>C(#N)C>[Br:24][C:12]1[S:11]/[C:10](=[CH:9]\[C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:22][CH3:23])=[O:21])/[N:14]([CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19]2)[C:13]=1[CH3:20]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69189523HCID 69189523, compound

Product 1

HCID 69188051HCID 69188051, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a 20 mL vial, a solution of Example 169B (620 mg, 1.772 mmol) was dissolved in acetonitrile (4 ml). N-bromosuccinimide (268 mg, 1.506 mmol) was added and the reaction was stirred for 16 hrs. The reaction was concentrated and purified by chromatography over silica gel (hex-EtOAc 4:1 as eluent) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.82-1.93 (m, 4 H) 1.95-2.06 (m, 2 H) 2.29 (s, 3 H) 2.71-2.84 (m, 1 H) 3.88 (s, 3 H) 4.06 (d, J=7.12 Hz, 2 H) 6.82 (s, 1 H) 7.14 (d, J=8.82 Hz, 1 H) 7.44 (dd, J=8.82, 2.71 Hz, 1 H) 7.66 (d, J=2.71 Hz, 1 H). MS (ESI) m/z 428 (M+H)+. Anal calcd for C19H22ClF2NO3S: C, 54.61; H, 5.31; N, 3.35. Found: C, 54.51; H, 5.26; N, 3.35.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by chromatography over silica gel (hex-EtOAc 4:1 as eluent)

Sources & evidence

ORD record
ord-653a89962a784f68908085ae22796e3d
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

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