Thionyl Chloride → HCID 9799587, compound

HRID 1075385Notes

Reaction equation

HRID 1075385 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[Cl:15][C:16]1[CH:17]=[C:18]([CH:27]=[CH:28][C:29]=1[NH2:30])[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>CN(C)C(=O)C>[C:19]([C:18]1[CH:27]=[CH:28][C:29]([NH:30][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])=[C:16]([Cl:15])[CH:17]=1)(=[O:20])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 347297NSC405902HCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid

Product 1

HCID 9799587HCID 9799587, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-17.5 °C

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.46 g) in N,N-dimethylacetamide (6 mL) was rapidly added thionyl chloride (0.35 g) and the mixture stirred at -15 to -20° C. for 1 hour. 3-Chloro-4-aminobenzophenone (0.45 g) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into ice water and filtered through diatomaceous earth. The diatomaceous earth was washed with methylene chloride, the organic solution dried and the solvent removed. Chromatography (eluent methylene chloride, then 5% ethyl acetate in methylene chloride) gave the title compound (0.31 g) as a white solid; mp 142-144° C. Analysis for C17H13ClF3NO3 : Calculated: C, 54.92; H, 3.53; N, 3.77; Found: C, 54.89; H, 3.63; N, 3.68.

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationfiltered through diatomaceous earth
  3. washThe diatomaceous earth was washed with methylene chloride
  4. customthe organic solution dried
  5. customthe solvent removed

Sources & evidence

ORD record
ord-397c61ac8ea2480ca3dbd325133298ae
Source dataset
uspto-grants-1999_05
Patent number
US05900432

Reaction notes

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