Formic Acid → HCID 44482293, compound

HRID 452612Notes

Reaction equation

HRID 452612 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1.[CH:21](O)=O>>[CH3:20][S:19][C:16]1[CH:17]=[CH:18][C:13]([N:12]2[C:3]3[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=3[N:1]=[CH:21]2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 44480700HCID 44480700, compound

Product 1

HCID 44482293HCID 44482293, compoundYield 74%

Procedure

A solution of methyl 4-amino-3-[[4-(methylthio)phenyl]amino]benzoate (5.78 g, 20.0 mmol) in formic acid (50 mL) was stirred at 100° C. overnight. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (4.44 g, yield 74%) as colorless crystals.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-845eb155ddb1485c858b650d5b2a4e00
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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