Dichloromethane → HCID 21898040, compound

HRID 1840855Notes

Reaction equation

HRID 1840855 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(N(CC)CC)C.[NH2:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH:34][S:35]([C:38]1[C:47]2[C:42](=[C:43]([N:48]([CH3:50])[CH3:49])[CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36].ClCCl>C1(C)C=CC=CC=1.C(O)C>[Cl:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([NH:23][CH2:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][CH2:33][NH:34][S:35]([C:38]2[C:47]3[C:42](=[C:43]([N:48]([CH3:50])[CH3:49])[CH:44]=[CH:45][CH:46]=3)[CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 27851382,4-Dichloro-3-nitroquinolineHCID 21898026HCID 21898026, compound

Product 1

HCID 21898040HCID 21898040, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
21 °C

Procedure

A solution of 2,4-dichloro-3-nitroquinoline (2.71 g, 0.0115 mole) in toluene (100 mL) was cooled to 0-5° C. in an ice bath. Triethylamine (1.5 g) was added in one portion. A solution of N-(10-amino-4,7-dioxadecyl)-5-dimethylaminonaphthalene-1-sulfonamide (4.6 g, 0.01159 mole) in toluene (60 mL) was added dropwise while maintaining the temperature below 10° C. The reaction was stirred at 2-5° C. for 4 hrs and at a room temperature of 21° C. overnight (18 hours). Thin layer chromatography (dichloromethane:ethanol) showed a trace of the amine starting material, but was mostly a bright yellow spot at the solvent front assumed to be the addition product. The toluene was removed by rotary evaporation to provide a viscous oil. The oil was purified by column chromatography (silica gel, dichloromethane/ethanol) to provide 2.4 g of N-[10-(2-chloro-3-nitro-4-quinolinyl)amino-4,7-dioxadecyl]-5-dimethylaminonaphthalene-1-sulfonamide.

Workup

  1. temperaturewhile maintaining the temperature below 10° C
  2. customThe toluene was removed by rotary evaporation
  3. customto provide a viscous oil
  4. customThe oil was purified by column chromatography (silica gel, dichloromethane/ethanol)

Sources & evidence

ORD record
ord-52c471d38dd448b7a208c4c34da42dbf
Source dataset
uspto-grants-2004_01
Patent number
US06683088B2

Reaction notes

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