Benzenamine, 3-chloro-N,N-diethyl-2,6-dinitro-4-(trifluoromethyl)- → HCID 20355154, compound

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Reaction Steps

The residue, which contained sodium pyrrolidone, was cooled to 40°, and a solution of 34.2 g of 2-chloro-4-diethylamino-3,5-dinitrobenzotrifluoride (0.1 m) in 50 cc of DMF was added in 0.5 hr. at 40°-46°. The reaction mixture was heated at 112°-115° for 21.5 hr., cooled, and partitioned between 100 cc of tolune and 200 cc of water. The toluene phase was given 5 × 100 cc water washes, and the toluene was removed by rotary evaporation, leaving 21.0 g of residue. The residue then was vacuum distilled using a micro short-path distillation apparatus. The product (5.5 g) distilled at 170°-180° (0.1-0.2 mm). The yellow distillate was recrystallized twice from 1 part of methanol to yield 2.2 g, 5.0% yield; mp 94°-95°; IR(KBr) 3080 (CH aromatic), 2990 (CH aliphatic), 1710 (C=O), 1530 and 1340 cm-1 (NO2); NMR (CDCl3) δ 8.1 (1, s, CH aromatic), 3.6 (2, t, CH2NCO), 3.1 (4, q NCH2 -CH3), 2.6-2.1 (4, m, CH2CH2C=O), 1.1 (6, t, CH3).

Provenance & Evidence