Hydrochloric Acid → HCID 20202968, compound

HRID 978420Notes

Reaction equation

HRID 978420 reaction equation
Cl.[N+:2]([C:5]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[C:13]([N+:20]([O-:22])=[O:21])[C:6]=1[NH:7][CH2:8][CH2:9][S:10][C:11]#[N:12])([O-:4])=[O:3]>C(O)C>[NH:12]=[C:11]1[N:7]([C:6]2[C:13]([N+:20]([O-:22])=[O:21])=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:5]=2[N+:2]([O-:4])=[O:3])[CH2:8][CH2:9][S:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20202945HCID 20202945, compound

Product 1

HCID 20202968HCID 20202968, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dry gaseous hydrogen chloride is introduced into 1.2 g (0.0038 moles) of 2,4,6-trinitro-N-(2-thiocyanatoethyl)-aniline in 120 ml of anhydrous ethanol for 5 hours, while the mixture is heated under reflux. The solvent is distilled off, the residue is boiled with 30 ml of ethyl acetate for 10 minutes, then the warm mixture is filtered. The insoluble matter is shaken with 30 ml of ethyl acetate and 20 ml of 10 percent aqueous sodium carbonate solution. The phases are separated, and the aqueous solution is extracted twice with 10 ml of ethyl acetate each time. The organic phases are combined, dried over anhydrous magnesium carbonate and evaporated. In this way 0.084 g (7%) of the title compound are obtained. M.p.: 160°-162° C. (ethyl acetate).

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. distillationThe solvent is distilled off
  4. filtrationthe warm mixture is filtered
  5. customThe phases are separated
  6. extractionthe aqueous solution is extracted twice with 10 ml of ethyl acetate each time
  7. dry with materialdried over anhydrous magnesium carbonate
  8. customevaporated

Sources & evidence

ORD record
ord-4645396c91a14c7288544415d0762fcf
Source dataset
uspto-grants-1987_05
Patent number
US04665083

Reaction notes

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