Cyclohexylamine → HCID 10634737, compound

HRID 1709214Notes

Reaction equation

HRID 1709214 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]1([NH2:18])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CN(C)C=O>[CH:12]1([NH:18][C:2]2[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 118992,4-Dichloronitrobenzene

Product 1

HCID 10634737HCID 10634737, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 15.09 g (78 mmol) 2,4-dichloronitrobenzen, 7,7 g (78 mmol) cyclohexylamine, 7.9 g (78 mmol) triethylamine and 100 ml dimethylformamide was stirred at 80° C. for 3 h. After cooling to 25° C. the mixture was evaporated, dissolved in 200 ml ether and filtered. The ether solution was washed with water and evaporated to the half volume. The precipitate was filtered off to give 3.8 g (19%) N-cyclohexyl-2-nitro5-chloraniline. M.p. 124.5° C. 1H-NMR (CDCl3): 8.2 (2H, m), 6.8 (1H, d), 6.5 (1H, dd), 3.5 (1H, broad s), 2.4-0.8 (1OH, m).

Workup

  1. temperatureAfter cooling to 25° C. the mixture
  2. customwas evaporated
  3. dissolutiondissolved in 200 ml ether
  4. filtrationfiltered
  5. washThe ether solution was washed with water
  6. customevaporated to the half volume
  7. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-5c9ec256693d439186445d824d2d25f5
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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