Formaldehyde → N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-(methylamino)benzamide

HRID 590941Notes

Reaction equation

HRID 590941 reaction equation
[NH2:1][C:2]1[C:3]([F:32])=[C:4]([CH:29]=[CH:30][CH:31]=1)[C:5]([NH:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:11]([C:18]([F:27])([C:23]([F:26])([F:25])[F:24])[C:19]([F:22])([F:21])[F:20])=[CH:10][C:9]=1[Br:28])=[O:6].S(=O)(=O)(O)O.[CH2:38]=O.[OH-].[Na+]>>[Br:28][C:9]1[CH:10]=[C:11]([C:18]([F:27])([C:19]([F:20])([F:21])[F:22])[C:23]([F:24])([F:25])[F:26])[CH:12]=[C:13]([C:14]([F:16])([F:17])[F:15])[C:8]=1[NH:7][C:5](=[O:6])[C:4]1[CH:29]=[CH:30][CH:31]=[C:2]([NH:1][CH3:38])[C:3]=1[F:32]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 866566853-amino-N-[2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluorobenzamide

Product 1

HCID 86656695N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-(methylamino)benzamideYield 72%

Procedure

0.930 g (1.71 mmol) of 3-amino-N-(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-2-fluorobenzamide was added to 5 ml of concentrated sulfuric acid, and 10 ml of a 37% aqueous formaldehyde solution was charged dropwise thereto at 40° C. The reaction mixture was poured into ice-water, adjusted to pH 10 using an aqueous sodium hydroxide solution, and extracted with the addition of ethyl acetate. The organic layer was washed with a 20% aqueous sodium hydroxide solution and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=8:1) to prepare 0.690 g (yield 72%) of a target compound.

Workup

  1. additionwas charged dropwise
  2. customat 40° C
  3. extractionextracted with the addition of ethyl acetate
  4. washThe organic layer was washed with a 20% aqueous sodium hydroxide solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (eluent solvent; hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-0e1c8e76aa1848b280930468c288bf25
Source dataset
uspto-grants-2016_01
Patent number
US09237745B2

Reaction notes

Loading…