Tin tetrachloride → HCID 22055247, compound

HRID 1829934Notes

Reaction equation

HRID 1829934 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:8]=1[C:9]#[N:10].[Sn](Cl)(Cl)(Cl)Cl>CCOC(C)=O>[NH2:15][C:12]1[CH:13]=[CH:14][C:7]([O:6][CH2:5][C:4]2[CH:18]=[CH:19][CH:20]=[C:2]([F:1])[CH:3]=2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

4

Reactant 2

HCID 24287Tin tetrachlorideHCID 22055254HCID 22055254, compound

Product 1

HCID 22055247HCID 22055247, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20A (108 mg, 0.4 mmol) and tin chloride (268 mg ,1.2 mmol) in EtOAc (4 ml) was heated to reflux for 15 h. The mixture was cooled to rt and triturated with EtOAc (2×60 ml). The filtrate was concentrated in vacuo. The combined EtOAc extracts were washed with NaHCO3 (1×30 ml), brine (1×30 ml), dried (MgSO4), filtered and concentrated in vacuo to give 20B (43 mg, 45% pure) which was used in next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 15 h
  3. customtriturated with EtOAc (2×60 ml)
  4. concentrationThe filtrate was concentrated in vacuo
  5. washThe combined EtOAc extracts were washed with NaHCO3 (1×30 ml), brine (1×30 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ecbf3ccba38413a8d295a30e004a20d
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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