Stannous chloride dihydrate → HCID 60208811, compound

HRID 2370658Notes

Reaction equation

HRID 2370658 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[Cl:14])[CH:2]=[CH2:3].O.O.[Sn](Cl)Cl>C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH2:1]([O:4][C:5]1[C:6]([Cl:14])=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 68195083HCID 68195083, compound

Product 1

HCID 60208811HCID 60208811, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of Example 278A (2 g, 10.35 mmol) in ethyl acetate (60 ml) added tin(II) chloride dihydrate (8.18 g, 36.2 mmol), and the mixture was heated at 65° C. overnight. The reaction mixture was cooled to room temperature, diluted with 100 mL ethyl acetate, and 1M aqueous Na2CO3 was added until precipitation stopped. The solid was filtered through a pad of diatomaceous earth. The filter pad was suspended in ethyl acetate, stirred for a few minutes, and rinsed with ethyl acetate. The filtrate was washed with saturated aqueous Na2CO3, water, and brine, dried over MgSO4, filtered, and concentrated. Chromatography was performed with an Analogix 280 with an SF 40-80 column, 0% to 5% methanol/dichloromethane gradient over 30 minutes to provide the title compound. MS (DCI+) m/z 164.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionwas added until precipitation
  3. filtrationThe solid was filtered through a pad of diatomaceous earth
  4. washrinsed with ethyl acetate
  5. washThe filtrate was washed with saturated aqueous Na2CO3, water, and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bc25fa315e984e08826b94a5fa2f74f3
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

Loading…