4-(4-nitro-phenyl)-3,6-dihydro-2H-thiopyran 1,1-dioxide → 4-(1,1-Dioxo-hexahydro-1lambda6-thiopyran-4-yl)-phenylamine

HRID 1428026Notes

Reaction equation

HRID 1428026 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][S:13](=[O:17])(=[O:16])[CH2:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[O:16]=[S:13]1(=[O:17])[CH2:14][CH2:15][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 591285764-(4-nitro-phenyl)-3,6-dihydro-2H-thiopyran 1,1-dioxide

Product 1

HCID 591285934-(1,1-Dioxo-hexahydro-1lambda6-thiopyran-4-yl)-phenylamineYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-nitro-phenyl)-3,6-dihydro-2H-thiopyran 1,1-dioxide (as prepared in the previous step, 502 mg, 1.98 mmol) and 10% Pd/C (250 mg, 50 wt %) in 15 mL of MeOH was stirred at RT under H2 (balloon pressure) for 2 h. The Pd catalyst was removed by filtration on Celite, and the filtrate was concentrated to give 314 mg (70%) of the title compound as a slightly yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 7.03 (d, 2H, J=8.3 Hz), 6.67 (d, 2H, J=8.3 Hz), 3.51-3.79 (br s, 2H), 3.11-3.17 (m, 4H), 2.70 (dddd, 1H, J=12.3, 12.3, 2.9, 2.9 Hz), 2.31-2.43 (m, 2H), 2.15-2.23 (m, 2H).

Workup

  1. customThe Pd catalyst was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3dad7a0ddd64415c8ff822aa5517299f
Source dataset
uspto-grants-2015_01
Patent number
US08933091B2

Reaction notes

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