Stannous chloride dihydrate → HCID 86641447, compound

HRID 1189946Notes

Reaction equation

HRID 1189946 reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]([F:24])([F:23])[C:8]([NH:10][CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=1)=[O:9]>C(O)C>[NH2:20][C:16]1[CH:15]=[C:14](/[CH:13]=[CH:12]/[CH2:11][NH:10][C:8](=[O:9])[C:7]([F:6])([F:23])[F:24])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 86641452HCID 86641452, compound

Product 1

HCID 86641447HCID 86641447, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride dihydrate (3.28 g, 14.5 mmol) was added to a solution of (E)-2,2,2-trifluoro-N-(3-(3-nitrophenyl)allyl)acetamide (1.0 g, 3.64 mmol) in ethanol. The reaction mixture was stirred under reflux overnight. The mixture was concentrated under reduced pressure to give dark brown viscous liquid. The reaction mixture was partitioned between sat NaHCO3 and EtOAc and then filtered through Celite which was thoroughly washed with ethyl acetate. Organic layer was separated and concentrated under reduced pressure to give (E)-N-(3-(3-aminophenyl)allyl)-2,2,2-trifluoroacetamide as a brown liquid. Yield (0.8 g, 89%); 1H NMR (400 MHz, DMSO-d6) δ 9.70 (bs, 1H), 6.96 (t, J=7.8 Hz, 1H), 6.51-6.60 (m, 2H), 6.45-6.48 (m, 1H), 6.39 (d, J=16.0 Hz, 1H), 6.05-6.10 (m, 1H), 5.07 (bs, 2H), 3.95 (t, J=5.6 Hz, 2H); ESI MS m/z 243.09 [M−H]+.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give dark brown viscous liquid
  4. customThe reaction mixture was partitioned
  5. filtrationfiltered through Celite which
  6. washwas thoroughly washed with ethyl acetate
  7. customOrganic layer was separated
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d21a7051301405bbcb14a899cfd7bf0
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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