Water → HCID 86607777, compound

HRID 1985669Notes

Reaction equation

HRID 1985669 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O.[O:19]=[C:20](Cl)OC(Cl)(Cl)Cl>O1CCOCC1>[CH3:17][N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[C:3]3[C:4]([O:6][C:20](=[O:19])[NH:1][C:2]3=[CH:10][CH:9]=2)=[O:5])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 509890072-AMino-5-(4-Methyl-1-piperazinyl)benzoic Acid

Product 1

HCID 86607777HCID 86607777, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 5.3 g of 2-amino-5-(4-methylpiperazino)benzoic acid in 30 mL of dioxane, under stirring and external cold water cooling 6 mL of diphosgene is added dropwise. The mixture is heated under reflux conditions for 4 hours. From the cold reaction mixture the solid material is filtered off, washed with 50 mL of ether. The product is stirred for 5 minutes in the mixture of 50 mL of methanol and 5 mL of triethylamine, filtered off, washed with 30 mL of methanol. After drying 5.4 g of the title product is obtained, m.p.: 285° C.

Workup

  1. temperatureThe mixture is heated under reflux conditions for 4 hours
  2. customFrom the cold reaction mixture the solid material
  3. filtrationis filtered off
  4. washwashed with 50 mL of ether
  5. stirringThe product is stirred for 5 minutes in the mixture of 50 mL of methanol and 5 mL of triethylamine
  6. filtrationfiltered off
  7. washwashed with 30 mL of methanol
  8. dry with materialAfter drying 5.4 g of the title product
  9. customis obtained

Sources & evidence

ORD record
ord-186b3899e251477585ac72f4473f4df1
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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