Hydrochloric Acid → N-(1-ethylpropyl)-3,4-dimethylaniline

HRID 2163624

Reaction equation

[N+]([C:4]1[C:15]([CH3:16])=[C:14]([CH3:17])[CH:13]=[C:12]([N+]([O-])=O)[C:5]=1[NH:6][CH:7]([CH2:10][CH3:11])[CH2:8][CH3:9])([O-])=O.[N+](C1C(C)=C(C)C=C([N+]([O-])=O)C=1N(N=O)C(CC)CC)([O-])=O.S(=O)(=O)(O)N.Cl>O.C(Cl)CCl>[CH2:8]([CH:7]([NH:6][C:5]1[CH:12]=[CH:13][C:14]([CH3:17])=[C:15]([CH3:16])[CH:4]=1)[CH2:10][CH3:11])[CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a crude nitration solution comprising 1550 g. of 2,6-dinitro-N-(1-ethylpropyl)-3,4-dimethylaniline and 340 g. of 2,6-dinitro-N-nitroso-N-(1-ethylpropyl)-3,4-dimethylaniline in 3700 mls. of ethylene dichloride was added 212 g. of sulfamic acid and 2850 mls. of 37.7% hydrochloric acid. The mixture was refluxed at 80° C. for six hours, 2-liters of water was added thereto and the aqueous phase was separated. The aqueous phase was extracted with 500 ml. of ethylene dichloride and the organic phases were combined. The combined organic phase was washed with 3-liters of water, the aqueous phase separated and the ethylene dichloride was removed under vacuum at 68° C. to recover 1915 g. of product containing 1820 g. of 2,6-dinitro-N-(1-ethylpropyl)-3,4-dimethylaniline and less than 0.1% of 2,6-dinitro-N-nitroso-N-(1-ethylpropyl)-3,4-dimethylaniline.

Workup

customthe aqueous phase was separated
extractionThe aqueous phase was extracted with 500 ml
washThe combined organic phase was washed with 3-liters of water
customthe aqueous phase separated
customthe ethylene dichloride was removed under vacuum at 68° C.
customto recover 1915 g
additionof product containing 1820 g

Sources & evidence

ORD record: ord-f3b71956e65b4282bb8923768fe552de
Source dataset: uspto-grants-1979_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04136117

Linked notes

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