Toluene → HCID 59150495, compound

HRID 1668582Notes

Reaction equation

HRID 1668582 reaction equation
CC([CH:5]1[C:11]2[CH:12]=[CH:13][C:14]([NH:16][C:17](=O)[CH3:18])=[CH:15][C:10]=2[CH2:9][CH2:8][N:7]([C:20]([O-:22])=[O:21])[CH2:6]1)(C)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1.C(OCC)(=O)C.C([O-])(O)=O.[Na+].[C:56]1([CH3:62])[CH:61]=CC=C[CH:57]=1>>[C:17]([NH:16][C:14]1[CH:13]=[CH:12][C:11]2[CH2:5][CH2:6][N:7]([C:20]([O:22][C:56]([CH3:62])([CH3:61])[CH3:57])=[O:21])[CH2:8][CH2:9][C:10]=2[CH:15]=1)(=[S:32])[CH3:18]

Participants

5

Reactant 4

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 86584982Sodium bicarbonate ethyl acetateHCID 86624111HCID 86624111, compound

Product 1

HCID 59150495HCID 59150495, compound

Procedure

1,1-dimethylethyl-7-(acetylamino)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (818 mg) and Lawesson's reagent (1.1 g) were combined in toluene (10 ml) and refluxed for 1.5 h. After cooling the reaction was worked up with ethyl acetate/NaHCO3 (sat. sol.). The combined organic layers were concentrated and the residue was purified by flash chromatography over silica gel, eluting with 40% ethyl acetate in hexane, affording the title compound (411 mg).

Workup

  1. temperaturerefluxed for 1.5 h
  2. temperatureAfter cooling the reaction
  3. concentrationThe combined organic layers were concentrated
  4. customthe residue was purified by flash chromatography over silica gel
  5. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-f9bcb7ba62be43229597b0e4717e5fee
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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