Formamide → HCID 136048871, compound

HRID 1720022Notes

Reaction equation

HRID 1720022 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=O)[C:13]([OH:19])([CH3:18])[C:14]([F:17])([F:16])[F:15])(O)=[O:2].C([NH2:23])=O>[Cl-].[Na+].O>[F:15][C:14]([F:17])([F:16])[C:13]([C:12]1[NH:23][C:1](=[O:2])[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([I:10])[CH:9]=2)[N:11]=1)([OH:19])[CH3:18]

Participants

4

Reactant 2

HCID 713FormamideHCID 22419839HCID 22419839, compound

Product 1

HCID 136048871HCID 136048871, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of N-(2-carboxy-4-iodophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide (5 g) and formamide (5 mL) was stirred and heated at 190°-200° C. for 3 hours. The cooled reaction mixture was poured into brine (150 mL) and extracted with ethyl acetate. The ethyl acetate solution was dried (Na2SO4) and evaporated. Chromatography, eluting with ethyl acetate, gave the title compound (2.86 g) as a white solid; mp 205°-207° C.; NMR: 1.75 (s,3), 7.48 (d,1), 7.5 (s,1), 8.13 (d,1), 8.42 (s,1), 12.05 (s,1); MS: m/z=385(M+1). Analysis for C11H8F3IN2O2 : Calculated: C, 34.40; H, 2.10; N, 7.29; Found: C, 34.48; H, 2.09; N, 7.26.

Workup

  1. temperatureheated at 190°-200° C. for 3 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried (Na2SO4)
  5. customevaporated
  6. washChromatography, eluting with ethyl acetate

Sources & evidence

ORD record
ord-a0828fce895a4748a2d503befff7f90d
Source dataset
uspto-grants-1996_04
Patent number
US05504089

Reaction notes

Loading…