Thionyl Chloride → HCID 10573268, compound

HRID 374876Notes

Reaction equation

HRID 374876 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.[CH3:15][O:16][C:17]1[CH:23]=[C:22]([S:24]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:21]=[CH:20][C:18]=1[NH2:19]>CN(C)C(=O)C>[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4]([NH:19][C:18]1[CH:20]=[CH:21][C:22]([S:24]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)(=[O:25])=[O:26])=[CH:23][C:17]=1[O:16][CH3:15])=[O:5]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 10754086HCID 10754086, compound

Product 1

HCID 10573268HCID 10573268, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (1.35 g) in N,N-dimethylacetamide (20 mL) was rapidly added thionyl chloride (1.01 g) and the mixture (a precipitate formed after a few minutes) was stirred at -15° to -5° C. for 1 hour. 2-Methoxy-4-(4-pyridylsulfonyl)aniline (1.50 g) was then added in one portion and the mixture allowed to stir at room temperature overnight. The solution was poured into ice water (200 mL) and the resulting tan solid was collected and recrystallized from absolute ethanol to yield the title compound as a white solid (1.58 g); mp 220°-222° C.; MS: 405(M+1); NMR (250 MHz): 1.53 (s,3,), 4.02 (s,3), 7.62 (d,1, J=1.9), 7.68 (dd,1, J=1.9, J=8.5), 7.92-7.95 (m,2,), 8.02 (s, 1,), 8.46 (d,1, J=10) 8.80-8.89 (m,2,), 9.90 (s,1,). Analysis for C16H15F3N2O5S: Calculated: C, 47.53; H, 3.74; N, 6.93; Found: C, 47.56; H, 3.77; N, 6.76.

Workup

  1. customthe mixture (a precipitate formed after a few minutes)
  2. stirringto stir at room temperature overnight
  3. customthe resulting tan solid was collected
  4. customrecrystallized from absolute ethanol

Sources & evidence

ORD record
ord-810e383459ff4faea0833a70d725137a
Source dataset
uspto-grants-1996_01
Patent number
US05482969

Reaction notes

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