Water → HCID 86607778, compound

HRID 1985691Notes

Reaction equation

HRID 1985691 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O.[O:25]=[C:26](Cl)OC(Cl)(Cl)Cl>O1CCOCC1>[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[C:3]3[C:4]([O:6][C:26](=[O:25])[NH:1][C:2]3=[CH:10][CH:9]=2)=[O:5])[CH2:12][CH2:13]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 66850696HCID 66850696, compound

Product 1

HCID 86607778HCID 86607778, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 15 g of 2-amino-5-(4-benzylpiperazin-1-yl)benzoic acid in 90 mL of dioxane, under stirring and external cold water cooling 12.7 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 120 mL of ether. The product is stirred for 5 minutes in the mixture of 100 mL of methanol and 10 mL of triethylamine, it is filtered off and washed with 50 mL of methanol. After drying 17 g of the title product is obtained, m.p.: 235° 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 120 mL of ether
  5. stirringThe product is stirred for 5 minutes in the mixture of 100 mL of methanol and 10 mL of triethylamine, it
  6. filtrationis filtered off
  7. washwashed with 50 mL of methanol
  8. dry with materialAfter drying 17 g of the title product
  9. customis obtained

Sources & evidence

ORD record
ord-37627006cb1b45019be0f2387a2e1430
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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