Phosphorus oxychloride → HCID 70536662, compound

HRID 2164820Notes

Reaction equation

HRID 2164820 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]2)=O)[NH:5][CH:6]=1.P(Cl)(Cl)(Cl)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39]>CC(C)=O.CCOCC>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39].[CH3:1][C:2]1[N:3]=[C:4]2[CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:14]=[C:15]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[N:5]2[CH:6]=1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 444266Maleic AcidHCID 178430864HCID 178430864, compound

Product 1

HCID 70536662HCID 70536662, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10 g of 1-[2-(4-methyl-2-imidazolylmethyl)phenylcarbamoyl]-4-methylpiperazine, 86 ml of phosphorous oxychloride and 7.24 g of phosphorous pentachloride is stirred at room temperature for 4 hours and evaporated to dryness. The residue is suspended in 186 ml of methylene chloride and 55.2 ml of triethylamine is added dropwise at 0° over a period of 15 minutes. The mixture is stirred at room temperature overnight, poured into cold water, basified with 10% aqueous potassium carbonate and extracted with methylene chloride. The methylene chloride extracts are re-extracted with 2N hydrochloric acid. The acidic extracts are basified with 2N aqueous sodium hydroxide and extracted three times with methylene chloride. The organic extracts are dried over magnesium sulfate, decolorized with charcoal and evaporated to dryness. The residue is chromatographed from 180 g of silica gel using methylene chloride-methanol-ammonium hydroxide (300:50:1) as eluant to give a foamy material which is dissolved in acetone and treated with an equivalent amount of maleic acid to give on dilution with ether the 2-methyl-5-(4-methyl-1-piperazinyl)-11H-imidazo[1,2-c][1,3]benzodiazepine mono-maleate, m.p. 195°-197°.

Workup

  1. customevaporated to dryness
  2. addition55.2 ml of triethylamine is added dropwise at 0° over a period of 15 minutes
  3. stirringThe mixture is stirred at room temperature overnight
  4. additionpoured into cold water
  5. extractionextracted with methylene chloride
  6. extractionThe methylene chloride extracts are re-extracted with 2N hydrochloric acid
  7. extractionextracted three times with methylene chloride
  8. dry with materialThe organic extracts are dried over magnesium sulfate
  9. customevaporated to dryness
  10. customThe residue is chromatographed from 180 g of silica gel
  11. customto give a foamy material which

Sources & evidence

ORD record
ord-a97fef51ddb84537811335001126c01d
Source dataset
uspto-grants-1985_03
Patent number
US04507311

Reaction notes

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