Sodium Bicarbonate → HCID 59864814, compound

HRID 2423273Notes

Reaction equation

HRID 2423273 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([OH:26])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:11]([N+:20]([O-])=O)=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH3:19])=[CH:13]2.O.O.[Sn](Cl)(Cl)(Cl)Cl.[C:34](=O)(O)[O-].[Na+]>CO>[NH2:20][C:11]1[C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:23][C:24]([O:26][CH3:34])=[O:25])=[CH:4][C:3]=2[O:2][CH3:1])=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:19])[NH:15]2

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 59864800HCID 59864800, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 59864814HCID 59864814, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 1.2 (1.00 g, 2.81 mmol) and tin chloride dihydrate (5.07 g, 22.5 mmol) dissolved in methanol (10 mL) was heated to 65° C. (external temperature, oil bath) overnight. The reaction solution was poured into aqueous 5% sodium bicarbonate solution and the resulting bi-phase passed through a pad of Celite, rinsing with water and ethyl acetate. The filtrate was separated and the organic layer washed with water and brine then stirred over magnesium sulfate, filtered and the filtrate concentrated in vacuo on a rotary evaporator to afford a yellow-green foamy solid. The product was isolated by chromatography on silica gel, eluting with ethyl acetate/hexane gradient, to afford a yellow foamy solid. LC-MS ESI (pos.) m/z: 341.2 (M+H).

Workup

  1. washrinsing with water and ethyl acetate
  2. customThe filtrate was separated
  3. washthe organic layer washed with water and brine
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo on a rotary evaporator
  6. customto afford a yellow-green foamy solid
  7. customThe product was isolated by chromatography on silica gel
  8. washeluting with ethyl acetate/hexane gradient
  9. customto afford a yellow foamy solid

Sources & evidence

ORD record
ord-c976512038e54f5ba861d71f261c9a13
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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