Hydrochloric Acid → HCID 70045047, compound

HRID 1378990Notes

Reaction equation

HRID 1378990 reaction equation
[OH-].[Na+].BrBr.[C:5]([C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)/[CH:11]=[CH:12]/[C:13]1[N:21]([CH3:22])[C:20]2[C:19](=[O:23])[N:18]([CH2:24][CH3:25])[C:17](=[O:26])[N:16]([CH2:27][CH3:28])[C:15]=2[N:14]=1)(=[O:7])C.S([O-])([O-])(=[O:34])=S.[Na+].[Na+].Cl>O1CCOCC1.O>[CH2:24]([N:18]1[C:19](=[O:23])[C:20]2[N:21]([CH3:22])[C:13](/[CH:12]=[CH:11]/[C:10]3[CH:29]=[CH:30][CH:31]=[C:8]([C:5]([OH:7])=[O:34])[CH:9]=3)=[N:14][C:15]=2[N:16]([CH2:27][CH3:28])[C:17]1=[O:26])[CH3:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 9842106HCID 9842106, compound

Product 1

HCID 70045047HCID 70045047, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Sodium hydroxide (432 mg, 10.8 mmol) and bromine (0.13 ml, 2.523 mmol) were added to water (3 ml) under ice-cooling, followed by addition of dioxane (3 ml). The mixture was slowly added to a suspension of 300 mg (0.819 mmol) of Compound 24 obtained in Example 23 in 3 ml of dioxane under ice-cooling, and the resulting mixture was stirred at room temperature for 3.5 hours. After ice-cooling, a 5% aqueous solution of sodium thiosulfate was added thereto, and the mixture was acidified with 2N HCl. The precipitated crystals were collected by filtration, and recrystallized from ethanol/water to give 254 mg (yield 84%) of Compound 25 as pale yellow needles.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureAfter ice-cooling
  4. filtrationThe precipitated crystals were collected by filtration
  5. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-4ad779e53850447297579fc319727a54
Source dataset
uspto-grants-1997_09
Patent number
US05670498

Reaction notes

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