Acetonitrile → HCID 54495584, compound

HRID 267330

Reaction equation

HRID 267330 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].Cl[C:18]1[C:19]([N+:47]([O-:49])=[O:48])=[C:20]([CH:30]=[CH:31][C:32]2[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][C:35]([N+:41]([O-:43])=[O:42])=[CH:34][C:33]=2[N+:44]([O-:46])=[O:45])[C:21]([N+:27]([O-:29])=[O:28])=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25].C(#N)C>CO>[N+:8]([C:7]1[CH:6]=[C:5]([N+:11]([O-:13])=[O:12])[CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]=1[CH2:1][C:22]1[C:21]([N+:27]([O-:29])=[O:28])=[C:20]([CH:30]=[CH:31][C:32]2[C:33]([N+:44]([O-:46])=[O:45])=[CH:34][C:35]([N+:41]([O-:43])=[O:42])=[CH:36][C:37]=2[N+:38]([O-:40])=[O:39])[C:19]([N+:47]([O-:49])=[O:48])=[CH:18][C:23]=1[N+:24]([O-:26])=[O:25])([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 83762,4,6-TrinitrotolueneHCID 3294692-Chloro-1,3,5-trinitro-4-[2-(2,4,6-trinitrophenyl)ethenyl]benzene

Product 1

HCID 54495584HCID 54495584, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction of 4.5 g (0.02 mole) of TNT with 4.6 g (0.01 mole) of 3-chloro-2,2',4,4',6,6'-hexanitrostilbene was carried out as in the above reactions. The crude reaction product, after extraction with methanol was a brittle mass which was dissolved in 50 mol of acetonitrile, diluted with an equal volume of methanol and heated on a hot plate with magnetic stirring. Light yellow crystals separated and were filtered off, washed well with methanol and dried. This material weighed 4.8 g, 71% of the theoretical yield, melted at 168°-170° (dec), and elemental analysis showed that it contained a mole of acetonitrile. Calcd for C23H12N10O18 : N, 19.6. Found: N, 19.7, 19.4. Recrystallized from 50 ml of THF with 50 ml of methanol added to the hot THF solution after filtering, the product separated in very fine, almost colorless crystals, mp 210°-211°C. Anal. Calcd for C21H9N9O18 : C, 37.2; H, 1.3; N, 18.8. Found: C, 37.5, 37.7; H, 1.6, 1.5; N, 19.0, 18.4.

Workup

  1. customThe crude reaction product
  2. extractionafter extraction with methanol
  3. temperatureheated on a hot plate with magnetic stirring
  4. customLight yellow crystals separated
  5. filtrationwere filtered off
  6. washwashed well with methanol
  7. customdried
  8. customRecrystallized from 50 ml of THF with 50 ml of methanol
  9. additionadded to the hot THF solution
  10. filtrationafter filtering
  11. customthe product separated in very fine, almost colorless crystals, mp 210°-211°C

Sources & evidence

ORD record
ord-2af45799271042048a33356e61663dfe
Source dataset
uspto-grants-1976_03
Patent number
US03941853

Linked notes

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