4-Chloro-1,2-dinitrobenzene → HCID 10730655, compound

HRID 1081459Notes

Reaction equation

HRID 1081459 reaction equation
[CH:1]1([CH2:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+]([O-])=O)([O-:11])=[O:10]>C(O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[C:13]([NH:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:14]=1

Participants

4

Reactant 2

HCID 330974-Chloro-1,2-dinitrobenzeneHCID 76688Cyclohexanemethylamine

Product 1

HCID 10730655HCID 10730655, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 13.6 g of cyclohexylmethylamine in 10 ml of 95° ethanol is added dropwise to a solution of 8.1 g of 1,2-dinitro-4-chlorobenzene in 20 ml of 95° ethanol. The temperature rises to 50° C. The reaction medium is stirred for 2 hours and the solvent is then evaporated off under vacuum. The residue is taken up with DCM, washed with water, then with 2N hydrochloric acid and then with water and dried over Na2SO4 and the solvent is then evaporated off under vacuum. The residue is chromatographed on silica using isopropyl ether as the eluent. 4.21 g of the expected product are obtained after recrystallization from heptane. M.p.=73° C.

Workup

  1. customrises to 50° C
  2. customthe solvent is then evaporated off under vacuum
  3. washwashed with water
  4. dry with materialwith 2N hydrochloric acid and then with water and dried over Na2SO4
  5. customthe solvent is then evaporated off under vacuum
  6. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-1f43a377ef5d4d019e9ec09e389e0936
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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