Bromine → HCID 70801736, compound

HRID 2038382Notes

Reaction equation

HRID 2038382 reaction equation
[Br:1]Br.C([O-])(=O)C.[K+].[C:8]([C:10]1[CH:11]=[C:12]([C:16]2[N:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[S:19][CH:20]=2)[CH:13]=[CH:14][CH:15]=1)#[N:9].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[Br:1][C:20]1[S:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:17][C:16]=1[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8]#[N:9])[CH:11]=1

Participants

6

Reactant 4

HCID 24408Bromine2×HCID 24477Sodium ThiosulfateHCID 517044Potassium Acetate2×HCID 63991321HCID 63991321, compound

Product 1

HCID 70801736HCID 70801736, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

At room temperature, 3.18 g (19.9 mmol) of bromine and 1.95 g (19.9 mmol) of potassium acetate are added to 1.03 g (3.98 mmol) of the compound from Example 34A in 50 ml of conc. acetic acid. The mixture is stirred at 100° C. for 12 h, whereby after 6 and 9 h the same amount of bromine (in each case 3.18 g, 19.9 mmol) and potassium acetate (in each case 1.95 g, 19.9 mmol) are again added. A 1M aqueous sodium thiosulfate solution is subsequently added, and the reaction solution is extracted with dichloromethane. The combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1→10:1). 1.15 g (86% of theory) of the title compound are obtained.

Workup

  1. extractionthe reaction solution is extracted with dichloromethane
  2. dry with materialThe combined organic phases are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record
ord-3b4d7af0da7d4bbc90478641a08882cb
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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