1,2,4-Trichlorobenzene → HCID 86742415, compound

HRID 622139Notes

Reaction equation

HRID 622139 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:14]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]3([CH:26]=[CH:25][C:24](=[O:27])[CH:23]=[CH:22]3)[N:11]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].ClC1C=CC(Cl)=CC=1Cl.[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39]>CC(C)=O>[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[C:37]([OH:42])(=[O:41])[C:38]([OH:40])=[O:39].[CH2:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]3[CH:26]=[CH:25][C:24](=[O:27])[CH:23]=[CH:22][C:12]3=[C:13]([S:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:14]=2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 131,2,4-TrichlorobenzeneHCID 971Oxalic AcidHCID 13691026HCID 13691026, compound

Product 1

HCID 86742415HCID 86742415, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

By working as in Example 5, but starting with 2-(4-allyl-1-piperazinyl)-4-phenylthio-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (15.2 g) and 1,2,4-trichlorobenzene (150 cc), a residue is obtained which is redissolved in chlorofrom (300 cc). The solution obtained is poured into silica (300 g) contained in a column 4.2 cm in diameter. Elution is first performed with chloroform (1 liter) and this eluate is rejected. Elution is then performed with a mixture of chloroform and methanol (90:10 by volume) (3 liters) and the corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue obtained is dissolved in acetone (15 cc). Oxalic acid (1.9 g), dissolved in acetone (15 cc), is added to the solution obtained. The precipitate formed is separated by filtration and washed with ethyl ether (10 cc). 3-(4-Allyl-1-piperazinyl)-1-phenylthio-7H-pyrrolo[1,2-a]azepin-7 -one dioxalate (2.45 g), m.p. 225° C., is thereby obtained.

Workup

  1. customa residue is obtained which
  2. dissolutionis redissolved in chlorofrom (300 cc)
  3. customThe solution obtained
  4. additionis poured into silica (300 g)
  5. washElution
  6. washElution
  7. additionis then performed with a mixture of chloroform and methanol (90:10 by volume) (3 liters)
  8. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  9. customThe residue obtained
  10. additionis added to the solution
  11. customobtained
  12. customThe precipitate formed
  13. customis separated by filtration
  14. washwashed with ethyl ether (10 cc)

Sources & evidence

ORD record
ord-454e5692092d4478a09a4490e0e7e6d5
Source dataset
uspto-grants-1988_09
Patent number
US04769366

Reaction notes

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