Ethyl Acetate → HCID 178503890, compound

HRID 342641Notes

Reaction equation

HRID 342641 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:5]=[C:6]([C@@H:14]([C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].[CH3:30][S:31][C:32](=[N:35][C:36]#[N:37])SC.C(OCC)(=O)C>C(O)C>[F:29][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([C@@H:14]([C:22]2[CH:23]=[CH:24][C:25]([NH:26][C:32](=[N:35][C:36]#[N:37])[S:31][CH3:30])=[CH:27][CH:28]=2)[CH2:15][C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:12])[F:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 22941422HCID 22941422, compound

Product 1

HCID 178503890HCID 178503890, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[1-(R)-(3,4 bis(difluoromethoxy)phenyl)-2-(4-pyridinyl)ethyl]aniline (1.8 g, 4.4 mmol) in ethanol (20 ml) at room temperature was added dimethylcyanodithioimidocarbonate (1.3 g, 8.9 mmol). The mixture was heated at 70° for 72 h, cooled and the solvent removed in vacuo to give a yellow foam. The foam was subjected to flash chromatography (SiO2 ; eluant ethyl acetate) to give the title compound as a yellow foam (1.2 g). 1Hnmr (300 MHz, CDCl3) δ 2.46 (3H, s), 3.30 (2H, d, J 7.98 Hz), 4.23 (1H, t, J 7.84 Hz), 6.46 (1H, t, J 73.58 Hz), 6.48 (1H, t, J 73.51 Hz), 6.90 (2H, d, J 6.0 Hz), 7.02 (1H, d, J 8.38 Hz), 7.06 (1H, br), 7.16 (1H, d, J 3.0 Hz), 7.16 (1H, d, J 3.0 z), 7.18-7.25 (3H, c), 8.10 (1H, br) and 8.40 (2H, d, J 6.03 Hz).

Workup

  1. temperatureThe mixture was heated at 70° for 72 h
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. customto give a yellow foam

Sources & evidence

ORD record
ord-2318036704c447deb01ed7f60fbeab96
Source dataset
uspto-grants-1999_01
Patent number
US05859034

Reaction notes

Loading…