1-Fluoro-2-nitrobenzene → HCID 14625401, compound

HRID 1639002Notes

Reaction equation

HRID 1639002 reaction equation
Cl.Cl.[C:3]1([N:9]2[CH2:15][CH2:14][NH:13][NH:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24].C(N(CC)C(C)C)(C)C>CN(C)C=O>[N+:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:13]1[CH2:14][CH2:15][N:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:10][CH2:11][NH:12]1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 23046774HCID 23046774, compound

Product 1

HCID 14625401HCID 14625401, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of hexahydro-5-phenyl-1H-1,2,5-triazepine dihydrochloride (15.0 g), 1-fluoro-2-nitrobenzene (9.48 ml), N,N-diisopropylethylamine (36.5 ml) in N,N-dimethylformamide (150 ml) was magnetically stirred and heated at 75°-80° for 5 hours under nitrogen. The solution was evaporated under oil pump vacuum and the residual syrup was mixed with chloroform and dilute sodium hydroxide. The aqueous phase was extracted once more with chloroform and the combined chloroform extracts were dried (MgSO4). The solution was evaporated to a syrup which was subjected to an oil pump vacuum. This material in benzene was applied to a column (80×4.0 cm) of dry column grade neutral alumina (Woelm) prepacked in benzene. Elution was with benzene and monitoring of fractions was by t.l.c. on Alox 25 uv254 plates (Brinkmann) with benzene as developer. The fractions containing the major component were evaporated to a syrup which was crystallized from benzeneheptane; wt. 13.82 g (78%), mp=118°-120°. Recrystallization from benzeneheptane gave pure titled product, mp=119° -121°.

Workup

  1. temperatureheated at 75°-80° for 5 hours under nitrogen
  2. customThe solution was evaporated under oil pump vacuum
  3. additionthe residual syrup was mixed with chloroform and dilute sodium hydroxide
  4. extractionThe aqueous phase was extracted once more with chloroform
  5. dry with materialthe combined chloroform extracts were dried (MgSO4)
  6. customThe solution was evaporated to a syrup which
  7. washElution
  8. additionThe fractions containing the major component
  9. customwere evaporated to a syrup which
  10. customwas crystallized from benzeneheptane
  11. customRecrystallization from benzeneheptane

Sources & evidence

ORD record
ord-ca65fb4a08e2456693df2070e72ad3b2
Source dataset
uspto-grants-1989_11
Patent number
US04882323

Reaction notes

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