Toluene → HCID 178518011, compound

HRID 1474040Notes

Reaction equation

HRID 1474040 reaction equation
[C:1](=[O:4])(O)O.[F:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[CH:8][C:7]=1[NH:14][C:15]([NH2:17])=[NH:16].[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[F:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[CH:8][C:7]=1[NH:14][C:15]1[N:17]=[C:1]([OH:4])[C:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C:18]=2[N:16]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 178512557HCID 178512557, compound

Product 1

HCID 178518011HCID 178518011, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2,3,4-Trifluorophenyl)guanidine carbonate (18.9 g, 100 mmol), β-keto esters (IV-1) (20.4 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 16.1 g of white solid (II-2) with yield of 54.6%.

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-d9ef3d66ff35414bb81c830873a29a5d
Source dataset
uspto-grants-2015_04
Patent number
US09018218B2

Reaction notes

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