Phosphorus sulfide (P2S5) → HCID 178441312, compound

HRID 76293Notes

Reaction equation

[CH2:1]([C:5]1=[CH:6][N:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[S:8]/[C:9]/1=[N:10]\[C:11](=O)[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[CH2:2][CH2:3][CH3:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>C1(C)C=CC=CC=1>[CH2:1]([C:5]1=[CH:6][N:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[S:8]/[C:9]/1=[N:10]\[C:11]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])=[S:27])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 82 °C

Procedure

To a solution of Example 1D (380 mg, 1 mmol) in toluene (25 mL) was added P2S5 (220 mg, 1 mmol) and the reaction mixture was heated at 82° C. for 75 minutes, concentrated under reduced pressure and purified via column chromatography (SiO2, 0-25% EtOAc in hexanes) to provide the title compound (0.14 g, 34% yield). 1H NMR (300 MHz, CDCl3) δ ppm 0.95 (t, J=7.3 Hz, 3 H), 1.40 (dd, J=15.1, 7.5 Hz, 2 H), 1.61-1.78 (m, 11 H), 2.84-3.00 (m, 2 H), 3.84 (s, 3 H), 6.90 (d, J=8.7 Hz, 1 H), 7.27-7.35 (m, 1 H), 7.66 (d, J=2.8 Hz, 1 H), 8.13 (s, 1 H). MS (DCI/NH3) m/z 398 (M+H)+.

Workup

concentrationconcentrated under reduced pressure
custompurified via column chromatography (SiO2, 0-25% EtOAc in hexanes)

Sources & evidence

ORD record: ord-5497dcda689d4ae1ba0c8f0736b1aa03
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835475B2

Reaction notes

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