Nitrogen → 5-(3-Chloro-5-nitrophenyl)thiazole

HRID 2375889Notes

Reaction equation

HRID 2375889 reaction equation
N#N.Cl[C:4]1[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[C:8]([Cl:10])[CH:9]=1.[S:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C([O-])(=O)C.[K+]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][C:8]1[CH:9]=[C:4]([C:18]2[S:14][CH:15]=[N:16][CH:17]=2)[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=1

Participants

7

Reactant 4

HCID 947NitrogenHCID 9256ThiazoleHCID 12064Benzene, 1,3-dichloro-5-nitro-HCID 517044Potassium Acetate

Product 1

HCID 587099825-(3-Chloro-5-nitrophenyl)thiazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

N2 was bubbled through a solution of 3,5-dichloronitrobenzene (0.384 g, 2.00 mmol), thiazole (0.204 g, 2.40 mmol), potassium acetate (0.294 g, 3.00 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.16 g, 0.14 mol) in DMF (5 mL) for 10 min. The mixture was then heated to 120° C. and stirred for 17 h. The solvents were removed in vacuo. The residue was purified by chromatography on silica gel (MeOH in methylene chloride: 1% to 5%) to afford the title compound. 1H-NMR (CDCl3, 400 MHz): δ=7.88 (t, J=2.0 Hz, 1H), 8.20 (t, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.32 (t, J=2.0 Hz, 1H), 8.90 (s, 1H). MS (ES+): m/z 241.04 (35Cl, MH+), 243.00 (37Cl, MH+). HPLC: tR=3.35 min (ZQ2000, polar—5 min).

Workup

  1. customThe solvents were removed in vacuo
  2. customThe residue was purified by chromatography on silica gel (MeOH in methylene chloride: 1% to 5%)

Sources & evidence

ORD record
ord-d8fac006903b495a88cf4adbf68ec1ed
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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