2,4,5-Trichloronitrobenzene → HCID 19438006, compound

HRID 1734655Notes

Reaction equation

HRID 1734655 reaction equation
Cl.[NH2:2][CH:3]1[CH2:7][CH2:6][CH:5]=[CH:4]1.[Cl:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12](Cl)=[CH:11][C:10]=1[Cl:19].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[Cl:8][C:9]1[C:10]([Cl:19])=[CH:11][C:12]([NH:2][CH:3]2[CH2:7][CH2:6][CH:5]=[CH:4]2)=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1

Participants

5

Reactant 3

HCID 69832,4,5-TrichloronitrobenzeneHCID 11430Potassium CarbonateHCID 135328392-cyclopenten-1-amine hydrochloride

Product 1

HCID 19438006HCID 19438006, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

3-Aminocyclopentene hydrochloride (R. Vince and S. Daluge, J. Med. Chem. 1974, 17,578) (5.10 g, 42.8 mmol), 1,2,4-trichloro-5-nitrobenzene (Aldrich, 10.0 g, 42.8 mmol), and potassium carbonate (98%, Aldrich, 15.00 g, 107 mmol) were refluxed in t-butyl alcohol (100 mL) under nitrogen for 24 hours. Volatiles were evaporated in vacuo and the residue chromatographed on silica gel. Title compound was eluted with 20-30% chloroform-hexanes as an orange powder (5.14 g, 44%), m.p. 85°-86° C.; 1H-NMR(DMSO-d6)δ: 8.27 (s, 1, aromatic CH), 7.88 (d, J=7.3 Hz, 1, NH), 7.48 (s, 1, aromatic CH), 6.2-6.0 (m, 1, =CH), 6.0-5.8 (m, 1, =CH), 5.0-4.7 (m, 1, NCH), 2.6-2.2 (m overlapping solvent, 3 CH), 1.8-1.5 (m, 1, 1/2CH2); mass spectrum(CI): 273 (M +1).

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue chromatographed on silica gel
  3. washTitle compound was eluted with 20-30% chloroform-hexanes as an orange powder (5.14 g, 44%), m.p. 85°-86° C.

Sources & evidence

ORD record
ord-60ba9b415730409d9526264688f4c53c
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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