HCID 4306769, compound → HCID 25130138, compound

HRID 1942987Notes

Reaction equation

HRID 1942987 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([NH:8][C:9]2[S:10][C:11]([C:15](=[O:17])[CH3:16])=[C:12]([CH3:14])[N:13]=2)[CH:7]=1.[Br-:20].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>Br.CC(O)=O>[Br:20][CH2:16][C:15]([C:11]1[S:10][C:9]([NH:8][C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:18][CH3:19])=[N:13][C:12]=1[CH3:14])=[O:17]

Participants

4

Reactant 2

HCID 4306769HCID 4306769, compoundHCID 21124087Pyridiniumtribromide

Product 1

HCID 25130138HCID 25130138, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

To a solution of 5z (0.15 g, 0.5 mmol) in HBr/HOAc (33% wt HBr in HOAc; 2.5 mL) was added pyridinium tribromide (0.18 g, 0.55 mmol). The reaction mixture was stirred at room temperature for 24 h and poured onto ice-water. The precipitated product was collected by filtration, washed with cold water, and dried to afford 6z (0.19 g, 99%). Rf=0.714 in Hexane:EtOAc:1:1. 1H NMR (600 MHz, DMSO-d6): δ 8.38 (d, J=2.4 Hz, 1H), 7.07-7.12 (m, 2H), 4.58 (s, 2H), 3.86 (s, 3H), 2.57 (s, 3H). 13C NMR (150 MHz, DMSO-d6): δ 183.1, 166.1, 158.1, 147.8, 129.8, 124.1, 123.1, 119.6, 119.4, 112.7, 56.2, 36.0, 18.7. MS m/z (ESI) 376.92 (M+H)+.

Workup

  1. additionpoured onto ice-water
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-76e7b9313b134a58a44f2f32123ec4e5
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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