4-Toluenesulfonyl chloride → HCID 10024938, compound

HRID 1371319Notes

Reaction equation

HRID 1371319 reaction equation
[OH-].[NH4+:2].[CH2:3]([C:7]1[N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:26])[C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:12]([O-])=[CH:11][C:10]=2[N:20]=1)[CH2:4][CH2:5][CH3:6].S(Cl)(C1C=CC(C)=CC=1)(=O)=O>ClCCl>[NH2:2][C:11]1[C:10]2[N:20]=[C:7]([CH2:3][CH2:4][CH2:5][CH3:6])[N:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:26])[C:9]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 22479020HCID 22479020, compound

Product 1

HCID 10024938HCID 10024938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Concentrated ammonium hydroxide (35 mL) was added with stirring to a solution of N-[3-(2-butyl-5-oxido-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-phenylurea (2.25 g, 5.39 mmol) in dichloromethane (100 mL). Tosyl chloride (1.13 g, 5.93 mmol) was added in small portions over a period of 30 minutes. After 1 hour the layers were separated. The aqueous layer was extracted with dichloromethane (2×25 mL). The organics were combined and extracted with water (3×50 mL). The aqueous layers were combined and filtered to provide 1.64 g of an off white solid. This material was recrystallized sequentially from 1,2-dichloroethane, isopropyl alcohol and methanol to provide 960 mg of N-[3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl]-N′-phenylurea as light tan needles, m.p. 191–192° C. Analysis: Calculated for C24H28N6O: % C, 69.21; % H, 6.78; % N, 20.18; Found: % C, 68.94; % H, 6.77; % N, 19.90.

Workup

  1. customAfter 1 hour the layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2×25 mL)
  3. extractionextracted with water (3×50 mL)
  4. filtrationfiltered
  5. customto provide 1.64 g of an off white solid
  6. customThis material was recrystallized sequentially from 1,2-dichloroethane, isopropyl alcohol and methanol

Sources & evidence

ORD record
ord-9318964fcb2144e3a3c82c90c532dad4
Source dataset
uspto-grants-2007_01
Patent number
US07157453B2

Reaction notes

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