Water → HCID 58552836, compound

HRID 520456Notes

Reaction equation

HRID 520456 reaction equation
S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[NH2:10][C:11]1[C:19]([C:20](=[O:23])[NH:21][CH3:22])=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O.O>CC(N(C)C)=O>[CH3:22][N:21]1[C:20](=[O:23])[C:19]2[C:11](=[C:12]([C:13]([OH:15])=[O:14])[CH:16]=[CH:17][CH:18]=2)[N:10]=[C:29]1[C:28]1[CH:31]=[CH:32][CH:33]=[C:26]([C:25]([F:24])([F:34])[F:35])[CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 679903-(Trifluoromethyl)benzaldehydeHCID 656671Sodium PyrosulfiteHCID 10397731HCID 10397731, compound

Product 1

HCID 58552836HCID 58552836, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

Sodium metabisulfite (3.56 g, 18.7 mmol) was added to a solution of 2-amino-3-(methylcarbamoyl)benzoic acid 31 (2.80 g, 14.4 mmol) and 3-(trifluoromethyl)benzaldehyde 32 (2.51 g, 14.4 mmol) in DMAC (45 mL). The reaction mixture was stirred at 100° C. for 21 h. H2O (150 mL) was added and the resulting precipitate was collected by filtration, rinsed with H2O and dried to give 33 (4.31 g, 84% yield).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washrinsed with H2O
  3. customdried

Sources & evidence

ORD record
ord-22950a1b5a4446c3aea8eddf2a6c2df5
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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