Tin tetrachloride dihydrate → HCID 68651299, compound

HRID 646705Notes

Reaction equation

HRID 646705 reaction equation
[N:1]([CH:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].O.O.[Sn](Cl)(Cl)(Cl)Cl>CO.C(OCC)(=O)C>[S:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[CH:4]([NH2:1])[CH2:5][CH2:6]2

Participants

5

Reactant 2

HCID 85782573Tin tetrachloride dihydrateHCID 86607835HCID 86607835, compound

Product 1

HCID 68651299HCID 68651299, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-(2-thienyl)-2,3-dihydro-1H-indene-1-yl)amine: To a solution of 2-(1-azido-2,3-dihydro-1H-indene-5-yl)thiophene (0.24 g, 0.99 mmol) in methanol (2mL) was added solid tin chloride dihydrate (0.45 g, 1.99 mmol) at room temperature under nitrogen. The reaction was stirred at room temperature overnight. The crude reaction mixture was poured into a separatory funnel and diluted with ethyl acetate (250 mL). The organic layer was washed with 2.0 N aqueous sodium hydroxide (50 mL), saturated aqueous sodium chloride (brine), and dried over anhydrous magnesium sulfate. Filtration, concentration and column chromatography on silica (9:1 dichloromethane/methanol) gave [5-(2-thienyl)-2,3-dihydro-1H-indene-1-yl]amine (0.15 g, 72% yield) as semi-solid: 1H NMR (400 MHz, CDCl3) 7.54 (m, 1H), 7.40 (d, 2H), 7.29 (m, 2H), 7.08 (m, 1H), 4.40 (t, 1H), 3.05 (m, 1H), 2.90 (m, 1H), 2.56 (m, 1H), 1.80 (m, 1H).

Workup

  1. customThe crude reaction mixture
  2. additionwas poured into a separatory funnel
  3. washThe organic layer was washed with 2.0 N aqueous sodium hydroxide (50 mL), saturated aqueous sodium chloride (brine)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationFiltration, concentration and column chromatography on silica (9:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-fcdb3d4a0b2242aea19f519ec1c47116
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

Loading…