Benzene, 1-(chloromethyl)-3,5-dinitro- → HCID 17902132, compound

HRID 2306537Notes

Reaction equation

HRID 2306537 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[Br-:15].[Na+].[CH3:17][C:18]1[C:26]([CH3:28])([CH3:27])[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([S:29]([OH:32])(=[O:31])=[O:30])[CH:24]=2)[N:19]=1.[K]>S1(CCCC1)(=O)=O.CC(C)=O>[Br-:15].[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH2:7][N+:19]1[C:20]2[C:25](=[CH:24][C:23]([S:29]([OH:32])(=[O:30])=[O:31])=[CH:22][CH:21]=2)[C:26]([CH3:28])([CH3:27])[C:18]=1[CH3:17])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 94673Benzene, 1-(chloromethyl)-3,5-dinitro-HCID 253881Sodium BromideHCID 5462222PotassiumHCID 11149656HCID 11149656, compound

Product 1

HCID 17902132HCID 17902132, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
100 °C

Procedure

3,5-Dinitrobenzyl chloride (22.1g, 102 mmol) and sodium bromide (10.5 g, 102 mmol) were added to 2,3,3-trimethyl-5-sulpho-indole, potassium salt (5.0 g, 20.4 mmol) in sulpholane (25 ml). The reaction mixture was stirred at 100° C. for 5 hours. The solution was then cooled to room temperature and acetone (300 ml) was added to the reaction flask. A brown precipitate was formed which was collected by filtration and then purified by reverse phase HPLC. This gave a beige solid which was dried in vacuo. UV (water/acetonitrile): λmax=283 nm. MS: m/z=420 (C18H18N3O7S=420.4).

Workup

  1. temperatureThe solution was then cooled to room temperature
  2. customA brown precipitate was formed which
  3. filtrationwas collected by filtration
  4. custompurified by reverse phase HPLC
  5. customThis gave a beige solid which
  6. customwas dried in vacuo

Sources & evidence

ORD record
ord-5c2b94a92b4847708caf741dd7894a09
Source dataset
uspto-grants-2004_12
Patent number
US06828116B1

Reaction notes

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