Thionyl Chloride → HCID 136048871, compound

HRID 1720023Notes

Reaction equation

HRID 1720023 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].S(Cl)(Cl)=O.OC(C(F)(F)F)(C)C(O)=O.IC1C=C(C(O)=O)C([NH2:45])=CC=1.C(=O)(O)[O-].[Na+]>CC(N(C)C)=O.O>[F:15][C:14]([F:17])([F:16])[C:13]([C:12]1[NH:45][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

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 72911Benzoic acid, 2-amino-5-iodo-HCID 516892Sodium BicarbonateHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 22419839HCID 22419839, compound

Product 1

HCID 136048871HCID 136048871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
-15 °C

Procedure

N-(2-Carboxy-4-iodophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide.Thionyl chloride (5 g) was slowly added to a stirred solution of 2-hydroxy-2-trifluoromethyl propionic acid (6.64 g) in dimethylacetamide (100 mL) cooled to and maintained at -15° C. After 1 hour, 5-iodoanthranilic acid (10 g) was added in one portion and the temperature was allowed to slowly rise to ambient temperature. After stirring overnight, the reaction mixture was poured into water (1500 mL). The aqueous mixture was treated with solid sodium bicarbonate to pH 4, filtered, washed (water), and dried to give the amide (13.1 g) as a tan solid; mp 240°-243° C. Leaching with cold methylene chloride raises the mp to 247°-250° C.; NMR: 1.58 (s,3), 7.74 (s,1), 7.96 (d,1), 8.28 (s,1), 8.45 (d,1), 12.28 (s,1); MS: m/z=404(M+1).

Workup

  1. temperaturecooled to and
  2. customto slowly rise to ambient temperature
  3. filtrationfiltered
  4. washwashed (water)
  5. customdried

Sources & evidence

ORD record
ord-0e803a58f5c34911aa8868ddea1b495e
Source dataset
uspto-grants-1996_04
Patent number
US05504089

Reaction notes

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