Phosphorus sulfide (P2S5) → 2-(3-Nitrophenyl)thiazolo[4,5-c]pyridine

HRID 419880Notes

Reaction equation

O[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21]>N1C=CC=CC=1.CC1C=CC(C)=CC=1>[N+:16]([C:12]1[CH:11]=[C:10]([C:9]2[S:21][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[N:8]=2)[CH:15]=[CH:14][CH:13]=1)([O-:18])=[O:17]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of N-(4-hydroxypyridin-3-yl)-3-nitrobenzamide (1.33 g, 5.2 mmol) and P2S5 (2.40 g, 10.4 mmol) in pyridine (6.0 mL) and p-xylene (24 mL) was stirred at 140° C. for 18 h. The solvent was removed under vacuo while hot and the residue was purified by recrystallization from EtOH to afford 2-(3-nitrophenyl)thiazolo[4,5-c]pyridine as a yellow solid (1.08 g, yield: 81%). MS (ESI) calcd. for C12H7N3O2S (m/z): 257, found: 258 [M+1]+.

Workup

customThe solvent was removed under vacuo while hot and the residue
customwas purified by recrystallization from EtOH

Sources & evidence

ORD record: ord-5a1303a7e9ab4bf3ba17dba67effe998
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093401B2

Reaction notes

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