Formamide → HCID 136093173, compound

HRID 1720024Notes

Reaction equation

HRID 1720024 reaction equation
C([O:4][C:5]([CH3:31])([C:27]([F:30])([F:29])[F:28])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:11][C:10]=1[C:24](O)=[O:25])=O)(=O)C.C([NH2:34])=O>O>[F:29][C:27]([F:28])([F:30])[C:5]([C:6]1[NH:34][C:24](=[O:25])[C:10]2[C:9](=[CH:14][CH:13]=[C:12]([S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:16])=[O:17])[CH:11]=2)[N:8]=1)([OH:4])[CH3:31]

Participants

4

Reactant 2

HCID 713FormamideHCID 22419847HCID 22419847, compound

Product 1

HCID 136093173HCID 136093173, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Acetoxy-N-(2-carboxy-4-phenylsulfonylphenyl)-3,3,3-trifluoro-2-methylpropionamide (100 mg) and formamide (2 mL) were mixed and heated at reflux for 1 hour. The reaction mixture was then cooled, poured into water and extracted with ethyl acetate. The ethyl acetate was washed (water, brine) dried (Na2SO4) and evaporated. The crude solid was treated with charcoal in ethyl acetate, and then crystallized from warm ethyl acetate by addition of hexanes to the cloud point, to give the title compound (69 mg) as white needles; mp 202°-204° C.; NMR: 1.73 (s,3), 7.62-7.73 (m,4), 7.86 (d,1), 8.01 (d,2), 8.27 (d,1), 8.59 (s,1); MS: m/z=399(M+1). Analysis for C17H13F3N2O4S.0.1 C4H8O2 : Calculated: C, 51.33; H, 3.42; N, 6.88; Found: C, 51.70; H, 3.58; N, 6.98.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction mixture was then cooled
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate was washed (water, brine)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. additionThe crude solid was treated with charcoal in ethyl acetate
  9. customcrystallized
  10. temperaturefrom warm ethyl acetate
  11. additionby addition of hexanes to the cloud point

Sources & evidence

ORD record
ord-fd9cde7b54c046d8863d1ab599a5dfe2
Source dataset
uspto-grants-1996_04
Patent number
US05504089

Reaction notes

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