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

HRID 371556Notes

Reaction equation

HRID 371556 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[Na].Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])[C:12]([N+:23]([O-:25])=[O:24])=[CH:11][C:10]=1[C:26]([F:29])([F:28])[F:27]>CN(C=O)C>[CH2:21]([N:18]([CH2:19][CH3:20])[C:13]1[C:12]([N+:23]([O-:25])=[O:24])=[C:11]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])[C:10]([C:26]([F:29])([F:28])[F:27])=[CH:9][C:14]=1[N+:15]([O-:17])=[O:16])[CH3:22]

Participants

4

Reactant 2

HCID 118978Benzenamine, 3-chloro-N,N-diethyl-2,6-dinitro-4-(trifluoromethyl)-HCID 67081631HCID 67081631, compound

Product 1

HCID 20355154HCID 20355154, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  1. temperaturewas cooled to 40°
  2. customat 40°-46°
  3. temperatureThe reaction mixture was heated at 112°-115° for 21.5 hr
  4. temperature, cooled
  5. custompartitioned between 100 cc of tolune and 200 cc of water
  6. customthe toluene was removed by rotary evaporation

Sources & evidence

ORD record
ord-dda3709b444440c4b56cb00022015612
Source dataset
uspto-grants-1978_05
Patent number
US04087270

Reaction notes

Loading…