Ammonia → HCID 9798742, compound

HRID 1108646Notes

Reaction equation

HRID 1108646 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:18]([O-])=[CH:17][C:16]=2[N:15]=[CH:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:27].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:27])[C:16]=2[N:15]=[CH:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 73974-Toluenesulfonyl chlorideHCID 18783935HCID 18783935, compound

Product 1

HCID 9798742HCID 9798742, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.87 g (44.52 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]quinoline-5-oxide was dissolved in 400 ml of methylene chloride and 200 ml of concentrated aqueous ammonia (29%) was added thereto under ice-cooling. A solution of p-toluenesulfonyl chloride (9.34 g, 48.98 mmol) in 50 ml of methylene was further added thereto and the mixture was stirred for 30 minutes, then rasing up to room temperature stirred for 2 hours. After the reaction solution was separated, the organic phase was washed with brine and dried (Na2SO4). The solvent was distilled off and the residue was triturated with chloroform, then collected by filtration to obtain 7.10 g (19.97 mmol) of 1-[4-(tert-butoxycarbonylamino)butyl]-1H-imidazo[4,5-c]-quinoline-4-amine shown below as a faint yellowish white solid. ##STR55## Its spectroscopic data are as follows: IR (KBr) cm-1 : 3440, 3380, 3110, 2980, 1710, 1650, 1530, 1260, 1160, 760.

Workup

  1. temperatureunder ice-cooling
  2. customrasing up to room temperature
  3. stirringstirred for 2 hours
  4. customAfter the reaction solution was separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. distillationThe solvent was distilled off
  8. customthe residue was triturated with chloroform
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-bf4d7c5cd5424e59bdd9cb930e65c342
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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