Toluene → HCID 178441157, compound

HRID 1474038Notes

Reaction equation

HRID 1474038 reaction equation
[C:1](=[O:4])(O)O.[C:5]1([NH:11][C:12]([NH2:14])=[NH:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:17]([C:16]1[C:1]([OH:4])=[N:13][C:12]([NH:11][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:14][C:15]=1[CH3:21])[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 1140TolueneHCID 16217093Carbonic acid, compound with phenylguanidine (1:1)

Product 1

HCID 178441157HCID 178441157, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenylguanidine carbonate (13.5 g, 100 mmol), β-keto esters (22.3 g, 120 mmol) and 120 mL of toluene were added to 250 mL of flask in sequence, the mixture was heated to reflux with a Dean Stark trap until all the water was removed, and continue refluxing for half an hour. After most of solvent was removed, the reaction solution was cooled to room temperature, the solid was filtered, washed with 20% ethanol aqueous solution and dried to obtain 18.3 g of white solid (II-1) with yield of 71.2%.

Workup

  1. temperaturethe mixture was heated
  2. customwas removed
  3. temperaturecontinue refluxing for half an hour
  4. customAfter most of solvent was removed
  5. filtrationthe solid was filtered
  6. washwashed with 20% ethanol aqueous solution
  7. customdried

Sources & evidence

ORD record
ord-9547a76e43dc488cb3b91aa3c4fac3aa
Source dataset
uspto-grants-2015_04
Patent number
US09018218B2

Reaction notes

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