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

HRID 1761707Notes

Reaction equation

HRID 1761707 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]>C(Cl)(Cl)Cl.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

6

Reactant 3

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

Product 1

HCID 86742415HCID 86742415, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6212ChloroformSolvent

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

Sources & evidence

ORD record
ord-895d7ccf9a744cdd8e6a296c1bd7e84c
Source dataset
uspto-grants-1989_05
Patent number
US04826974

Reaction notes

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