Methane → HCID 13015160, compound

HRID 1106014Notes

Reaction equation

HRID 1106014 reaction equation
[F:1][C:2]([N+:17]([O-:19])=[O:18])([N+:14]([O-:16])=[O:15])[CH2:3][NH:4][CH2:5][C:6]([N+:11]([O-:13])=[O:12])([N+:8]([O-:10])=[O:9])[F:7].C(Cl)(Cl)Cl.Cl[C:25]1C=[CH:28][S:27][C:26]=1C(OCC)=O.C.C[OH:37]>[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]([N+:17]([O-:19])=[O:18])([N+:14]([O-:16])=[O:15])[CH2:3][N:4]([CH2:5][C:6]([N+:11]([O-:13])=[O:12])([N+:8]([O-:10])=[O:9])[F:7])[C:28](=[O:37])[S:27][CH2:26][CH3:25]

Participants

7

Reactant 5

HCID 297MethaneHCID 887MethanolHCID 6212Chloroform2×HCID 1403382-Fluoro-N-(2-fluoro-2,2-dinitroethyl)-2,2-dinitro-ethylamineHCID 12993676Ethyl 3-chlorothiophene-2-carboxylate

Product 1

HCID 13015160HCID 13015160, compound

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

A mixture of 55.0 g (0.19 mol) of bis(2-fluoro-2,2-dinitroethyl)amine, 38 ml of chloroform, 40 ml of ethyl chlorothiolformate and 20 ml of titanium tetrachloride was heated in an oil bath at 65°-67° C. for 17 hours (The reaction mixture was protected from atmospheric moisture with a drierite drying tube). Chloroform (100 ml) was added to the warm mixture which was then filtered through celite. The dark colored filtrate was pulled on a rotary evaporator to give a residue which was dissolved in methanol and treated with charcoal. After filtration, the solvent was removed with a rotary evaporator and the product was crystallized by dissolving in chloroform (55 ml) and cooling in the freezer. The yield was 48.0 g (67%), mp 74°-75° C., NMR (chloroform): δ1.26(t), 2.95(q), 4.83(d).

Workup

  1. temperaturewas heated in an oil bath at 65°-67° C. for 17 hours (The reaction mixture
  2. customwas protected from atmospheric moisture with a drierite drying tube
  3. filtrationwas then filtered through celite
  4. customThe dark colored filtrate was pulled on a rotary evaporator
  5. customto give a residue which
  6. filtrationAfter filtration
  7. customthe solvent was removed with a rotary evaporator
  8. customthe product was crystallized
  9. dissolutionby dissolving in chloroform (55 ml)
  10. temperaturecooling in the freezer

Sources & evidence

ORD record
ord-f08df5c39d8c4745816ac1fdd182e6d2
Source dataset
uspto-grants-1982_01
Patent number
US04311649

Reaction notes

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