Bromine → HCID 25130824, compound

HRID 1942992Notes

Reaction equation

HRID 1942992 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:9](=[O:12])[CH2:10][CH3:11])=[C:5]([CH2:7][CH3:8])[N:6]=1.[Br:13]Br>C(O)(=O)C>[NH2:1][C:2]1[S:3][C:4]([C:9](=[O:12])[CH:10]([Br:13])[CH3:11])=[C:5]([CH2:7][CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 12709877HCID 12709877, compound

Product 1

HCID 25130824HCID 25130824, compoundYield 112.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 14z (0.53 g, 1.99 mmol; HBr form) in acetic acid (2 mL) was treated dropwise with bromine (103 μL, 1.99 mmol), and the reaction mixture was stirred at room temperature for 3 h. The white precipitate was collected by filtration and washed with cold acetone to yield 15z as a white powder (0.59 g, 86%). Mp decomposition at 122° C. 1H NMR (600 MHz, DMSO-d6): δ 4.99 (q, J=6 Hz, 1H), 2.88 (q, J=6 Hz, 2H), 1.69 (d, J=6 Hz, 3H), 1.16 (t, J=6 Hz, 3H). 13C NMR (150 MHz, DMSO-d6): δ 185.5, 170.7, 115.5×2, 47.6, 47.5, 24.0, 20.8, 13.5. MS m/z (ESI) 263.00 [M+H]+, 264.96 [(M+2)+H]+.

Workup

  1. filtrationThe white precipitate was collected by filtration
  2. washwashed with cold acetone

Sources & evidence

ORD record
ord-0de538caa1474a6c8ae7b41465a422c8
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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