Hydrogen Bromide → HCID 178432529, compound

HRID 1020892Notes

Reaction equation

FC(F)(F)S([O-])(=O)=O.[Cl:9][C:10]1[C:30]([Cl:31])=[CH:29][C:13]2[N+:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[C:15]([CH3:18])[N:16]([CH3:17])[C:12]=2[CH:11]=1.[BrH:32]>>[Br-:32].[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N+:14]1[C:13]2[CH:29]=[C:30]([Cl:31])[C:10]([Cl:9])=[CH:11][C:12]=2[N:16]([CH3:17])[C:15]=1[CH3:18])([OH:26])=[O:25]

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 178471416HCID 178471416, compound

Product 1

HCID 178432529HCID 178432529, compoundYield 77%

Conditions

Temperature: 65 °C

Procedure

5 (4 g) was dissolved in 48% HBr aqueous solution (5 mL) and heated at 65° C. for 2 hrs and then evaporated to dryness. The residue was recrystalized from acetone to yield 2.5 g white crystal, yield 77%. See FIG. 12. 1H NMR: (DMSO) 1.36 (m, 2H), 1.54 (m, 2H), 1.74 (m, 2H), 2.21 (t, 2H), 2.87 (s, 3H), 3.95 (s, 3H), 4.46 (t, 2H), 8.49 (s, 1H), 8.54 (s, 1H). 13C NMR: (DMSO): 10.75, 23.92, 25.14, 28.19, 32.08, 33.37, 45.13, 114.78, 114.82, 128.73, 128.76, 130.04, 130.91, 154.26, 174.20. ESI-MS (m/z) calcd (found): 329.1 (329.1) for [M]+.

Workup

customevaporated to dryness
customThe residue was recrystalized from acetone

Sources & evidence

ORD record: ord-4b668ee906704f30b8a6b6032a90e032
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716491B2

Reaction notes

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