Acetone → HCID 22619798, compound

HRID 840564Notes

Reaction equation

HRID 840564 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([NH:11][CH:12]2[CH2:14][CH2:13]2)[CH:3]=1.ClC1C=CC(N)=C(N[CH:24]2[CH2:26][CH2:25]2)C=1.C(Cl)(Cl)Cl.C[C:32](C)=[O:33].[OH-].[Na+]>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([NH:8][C:26]([CH3:24])([CH3:25])[C:32](=[O:33])[N:11]2[CH:12]2[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 2921984HCID 2921984, compoundHCID 22619782HCID 22619782, compound

Product 1

HCID 22619798HCID 22619798, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

4-Chloro-2-cyclopropylaminonitrobenzene (2.0 g, 9.4 mmol) was hydrogenated as described in Example XVIIIA. The resulting 4-chloro-2-cyclopropylaminoaniline (1.70 g) was taken up in 20 ml of dichloromethane. 1.6 ml (2.01 mmol) of chloroform, 1.8 ml (2.45 mmol) of acetone and 0.10 g (0.4 mmol) of benzyltriethylammonium chloride were added, and the reaction solution was cooled to 10° C. 4 ml of 50% strength sodium hydroxide solution were slowly added dropwise with vigorous stirring, during which process the reaction temperature should not exceed 10° C. After stirring for 5 hours at 10° C., the phases were diluted and separated. The organic phase was washed once with water, dried (magnesium sulfate) and evaporated in vacuo. The crude product was purified by silica gel chromatography using ethyl acetate/heptane=1:2 as the eluent. The yield was 1.0 g (42%) of white crystals of melting point 132-133° C. (after recrystallization from toluene/heptane).

Workup

  1. customexceed 10° C
  2. additionthe phases were diluted
  3. customseparated
  4. washThe organic phase was washed once with water
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. customThe yield was 1.0 g (42%) of white crystals of melting point 132-133° C. (after recrystallization from toluene/heptane)

Sources & evidence

ORD record
ord-5c205923ac8e40f0a321ddf10c9e738f
Source dataset
uspto-grants-2002_04
Patent number
US06369057B1

Reaction notes

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