Hydrochloric Acid → HCID 59864880, compound

HRID 2423279Notes

Reaction equation

HRID 2423279 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[C:6]([N+:26]([O-])=O)[C:7]([O:11][C:12]3[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][C:13]=3[O:24][CH3:25])=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:29].O.O.[Sn](Cl)(Cl)(Cl)Cl.Cl>C(OCC)(=O)C>[NH2:26][C:6]1[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:14][C:13]=2[O:24][CH3:25])=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[C:3]([CH3:29])[N:2]2[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59864847HCID 59864847, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59864880HCID 59864880, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3.2 (35 mg, 0.088 mmol) and tin chloride dihydrate (159 mg, 0.70 mmol) dissolved in ethyl acetate (5 mL) was heated to 80° C. overnight. Alter 18 h, HPLC indicated no 3.2 remained and the reaction was poured into aqueous 5% hydrochloric acid solution. The resulting emulsion was filtered through a pad of Celite to remove fine solids, rinsing the solids with ethyl acetate and water. The biphasic filtrate was separated and the organic layer washed with saturated aqueous sodium bicarbonate solution, water and brine. The organic separation was stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a dark brown, foamy solid.

Workup

  1. filtrationThe resulting emulsion was filtered through a pad of Celite
  2. customto remove fine solids
  3. washrinsing the solids with ethyl acetate and water
  4. customThe biphasic filtrate was separated
  5. washthe organic layer washed with saturated aqueous sodium bicarbonate solution, water and brine
  6. customThe organic separation
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  9. customto afford a dark brown, foamy solid

Sources & evidence

ORD record
ord-d4af39c6392b4eb69efb679f5023d961
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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