Dimethylformamide → N-(2-Chloroethyl)-2,6-dinitro-N-2-propen-1-yl-4-(trifluoromethyl)benzenamine

HRID 441785Notes

Reaction equation

HRID 441785 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:21][CH:22]=[CH2:23])[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19].CN(C)C=O.S(Cl)([Cl:31])=O>C1C=CC=CC=1>[Cl:31][CH2:2][CH2:3][N:4]([CH2:21][CH:22]=[CH2:23])[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:6]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 53750272HCID 53750272, compound

Product 1

HCID 53970178N-(2-Chloroethyl)-2,6-dinitro-N-2-propen-1-yl-4-(trifluoromethyl)benzenamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

16.7 parts by weight of N-hydroxyethyl-N-allyl-2,6-dinitro-4-trifluoromethylaniline is dissolved in 50 parts by weight of benzene. After adding 1 part by weight of dimethylformamide and dripping in 30 parts by weight of thionyl chloride at room temperature the whole is boiled for two hours under reflux. The volatile constituents are distilled off from the reaction mixture at 20 mm Hg, the residue is taken up in ethyl acetate, the solution is washed with ice-water, then with 10% sodium bicarbonate solution and finally again with water and the organic phase is dried over sodium sulfate.

Workup

  1. temperatureunder reflux
  2. distillationThe volatile constituents are distilled off from the reaction mixture at 20 mm Hg
  3. washthe solution is washed with ice-water
  4. dry with materialwith 10% sodium bicarbonate solution and finally again with water and the organic phase is dried over sodium sulfate

Sources & evidence

ORD record
ord-7a6ede6311244f36bf73244151260b1e
Source dataset
uspto-grants-1977_08
Patent number
US04042628

Reaction notes

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