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p-Toluenesulfonic acid → HCID 178498283, compound

HRID 349491
Notes
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Reaction equation

HRID 349491 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH2:23])[CH:16]=1.[Cl:25][C:26]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].C([O-])(O)=O.[Na+]>>[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH:23][C:28](=[NH:29])[C:27]2[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:26]=2[Cl:25])[CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 1090002-Chloro-4-fluorobenzonitrileHCID 516892Sodium BicarbonateHCID 2734814Methyl 3-Amino-4-methoxybenzoate

Product 1

HCID 178498283HCID 178498283, compoundYield 72%

Conditions

Temperature
160 °C

Procedure

Anhydrous p-toluene sulfonic acid (41.99 g, 220.76 mmol) was melted at 120° C. and 3-amino-4-methoxy benzoic acid methyl ester (20 g, 110.38 mmol) obtained in step 1 of Preparation Example 1 and 2-chloro-4-fluorobenzonitrile (25.76 g, 165.57 mol) were added thereto and stirred at 160° C. for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (26.70 g, 79.47 mmol) in a yield of 72%.

Workup

  1. additionwere added
  2. temperatureThe resulting solution was cooled to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-95a8d94956b34dcba86f71aa22bf6a89
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07179832B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes