2-Pentanamine → N-(1-methylbutyl)-4-(methylsulfonyl)-2,6-dinitro-m-toluidine

HRID 903483Notes

Reaction equation

HRID 903483 reaction equation
Cl[C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([CH3:15])[C:5]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[NH2:19][CH:20]([CH2:22][CH2:23][CH3:24])[CH3:21]>C1C=CC=CC=1>[CH3:21][CH:20]([NH:19][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([S:11]([CH3:14])(=[O:13])=[O:12])=[C:4]([CH3:15])[C:3]=1[N+:16]([O-:18])=[O:17])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 122462-PentanamineHCID 233359733-Chloro-6-(methylsulfonyl)-2,4-dinitrotoluene

Product 1

HCID 23335968N-(1-methylbutyl)-4-(methylsulfonyl)-2,6-dinitro-m-toluidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-chloro-6-(methylsulfonyl)-2,4-di-nitrotoluene (10.0 g., 0.034 mole) and 2-aminopentane (6.1 g. 0.07 mole) is refluxed in benzene (75 ml.) for 4 hours. After standing overnight, the mixture is successively washed with dilute hydrochloric acid, water, a 5% aqueous potassium carbonate solution and finally water. The mixture is then dried over magnesium sulfate. Removal of the magnesium sulfate and solvent leaves the desired product as a yellow oil which readily crystallized on cooling. The crude product is recrystallized from ethanol to give 9.5 grams with m.p. 85°-88° C.

Workup

  1. washthe mixture is successively washed with dilute hydrochloric acid, water
  2. dry with materialThe mixture is then dried over magnesium sulfate
  3. customRemoval of the magnesium sulfate and solvent

Sources & evidence

ORD record
ord-894ae7259c644d92a7d8c2883be4ed37
Source dataset
uspto-grants-1980_10
Patent number
US04227913

Reaction notes

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