Phosphorus sulfide (P2S5) → HCID 44553395, compound

HRID 1254042Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:32]=[CH:31][C:24]([C:25]([NH:27][NH:28][CH:29]=O)=O)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:34]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[N:11][C:10]=2[C:21]2[CH:32]=[CH:31][C:24]([C:25]3[S:34][CH:29]=[N:28][N:27]=3)=[CH:23][CH:22]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

4-{5-[(4-Chlorophenyl)thio]-1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl}-N′-formylbenzohydrazide (Example 49, 450 mg, 0.98 mmol) was treated with P2S5 (218 mg, 0.98 mmol) in 12 mL of dioxane. After the reaction mixture was heated at 55° C. overnight, the volatiles were removed in vacuo. The residue was diluted with EtOAc, washed with 1N NaOH, water, and brine. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was subjected to silica gel column chromatography eluting with 30-85% EtOAc in hexanes to afford the title compound. 1H NMR (500 MHz, (CDCl3): 9.13 (s, 1H), 8.67 (d, 1H), 8.43 (broad d, 1H), 8.38 (d, 2H), 8.06 (d, 2H), 7.89 (t, 1H), 7.39 (t, 1H), 7.25 (d, 2H), 7.04 (d, 2H), 4.16 (s, 3H). LCMS: m/z 462 (M+H)+.

Workup

customthe volatiles were removed in vacuo
additionThe residue was diluted with EtOAc
washwashed with 1N NaOH, water, and brine
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
washeluting with 30-85% EtOAc in hexanes

Sources & evidence

ORD record: ord-dece03a0844f4d25a8dcc81c23880627
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455528B2

Reaction notes

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