Sec-Butylamine → HCID 12767738, compound

HRID 2398696Notes

Reaction equation

HRID 2398696 reaction equation
Cl[C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[CH:4][C:5]([C:12]([F:15])([F:14])[F:13])=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9].[CH:19]([NH2:23])([CH2:21][CH3:22])[CH3:20]>C1C=CC=CC=1>[CH:19]([NH:23][C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[CH:4][C:5]([C:12]([F:15])([F:14])[F:13])=[C:6]([CH3:11])[C:7]=1[N+:8]([O-:10])=[O:9])([CH2:21][CH3:22])[CH3:20]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 20272574HCID 20272574, compound

Product 1

HCID 12767738HCID 12767738, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A nitration mixture, consisting of 16.1 ml. of H2SO4 (d 1.84) and 1.9 ml. of HNO3 (d 1.5), is heated to 55° C. and 3.5 grams of 5-chloro-2-(trifluoromethyl)toluene is slowly added. The mixture is heated for one hour at 55° C. followed by one hour at 110° C. The reaction mixture is cooled and poured onto ice to give 5-chloro-2-(trifluoromethyl)-4,5-dinitrotoluene as a cream-colored solid. The product is crystallized from cyclohexane to give 3.6 grams of cream-colored crystals, melting point 81° C. to 82° C. 1.8 Grams of 5-chloro-2-(trifluoromethyl)-4,6-dinitrotoluene is refluxed for 15 minutes with 3 ml. of mono-sec-butylamine and 30 ml. of benzene, cooled, filtered, washed with water until neutral, dried and vacuum stripped to give 1.5 grams of N-sec-butyl-3-methyl-2,6-dinitro-4-(trifluoromethyl)aniline as a yellow solid, melting point 38° C. to 39° C.

Workup

  1. filtrationfiltered
  2. washwashed with water until neutral,
  3. customdried

Sources & evidence

ORD record
ord-9952661733d74f31835f28f35bdeaadf
Source dataset
uspto-grants-1977_05
Patent number
US04025538

Reaction notes

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