2,4,5-Trichloronitrobenzene → HCID 67654434, compound

HRID 1734635Notes

Reaction equation

HRID 1734635 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][CH:4]([OH:7])[CH:3]1[OH:8].[Cl:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[C:13](Cl)=[CH:12][C:11]=1[Cl:20].C(N(CC)CC)C>C(O)(C)(C)C>[Cl:9][C:10]1[C:11]([Cl:20])=[CH:12][C:13]([NH:1][CH:2]2[CH2:6][CH2:5][CH:4]([OH:7])[CH:3]2[OH:8])=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1

Participants

5

Reactant 3

HCID 69832,4,5-TrichloronitrobenzeneHCID 8471TriethylamineHCID 13497972rac-(1R,2R,3S)-3-Amino-1,2-cyclopentanediol

Product 1

HCID 67654434HCID 67654434, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

(±)-(1R*, 2S*, 3R*)-3-Amino-1,2-cyclopentanediol (7.10 g, 50.0 mmol), 1,2,4-trichloro-5-nitrobenzene (11.67 g, 50.0 mmol as 97%, Aldrich), triethylamine (10 mL) and t-butanol (50 mL) were refluxed under nitrogen for 7 hours. Volatiles were removed in vacuo and the black residue chromatographed on silica gel. Title compound was eluted with methanol:chloroform/1:24 as an orange solid (6.45 g, 42%). Crystallization of such a sample from ethanol-water gave title compound as yellow needles, m.p. 137°-140° C.; 1H-NMR (DMSO-d6)δ: 8.26 and 7.49 (both s, 1 each, 2 aromatic CH), 8.06 (d, J=7.0 Hz, 1, NH), 5.04 (d, J=6.1 Hz, 1, OH), 4.65 (d, J=4.1 Hz, 1, OH), 4.0-3.7 (m, 3, 2 OCH and NCH), 2.2-2.21, 2.0-1.8, 1.7 -1.3 (all m, 4, 4 CH).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe black residue chromatographed on silica gel
  3. washTitle compound was eluted with methanol
  4. customCrystallization of such a sample from ethanol-water

Sources & evidence

ORD record
ord-b5f0ef754d1349e7ba0e4a67efd0a6dc
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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