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Sodium Hydroxide → HCID 11596645, compound

HRID 1075382
Notes
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Reaction equation

HRID 1075382 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[C:21]([NH2:22])=[CH:20][C:19]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:18][CH:17]=1.[OH-].[Na+]>CN(C)C(=O)C>[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4]([NH:22][C:21]1[C:16]([Cl:15])=[CH:17][CH:18]=[C:19]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:20]=1)=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 30207732-Chloro-5-(phenylsulphonyl)aniline

Product 1

HCID 11596645HCID 11596645, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Conditions

Temperature
-20 °C

Procedure

To a solution containing 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (2.00 g) in N,N-dimethylacetamide (40 mL) cooled to -20° C. was added thionyl chloride (1.50 g) and the mixture was stirred for 1.0 hour. 6-chloro-3-phenylsulfonylaniline (2.42 g) was added in one portion and mixture was stirred for 48 hours at room temperature. The reaction mixture was poured into aqueous sodium hydroxide (1.0 N, 250 mL) and extracted with ethyl acetate. The combined ethyl acetate extracts were washed (aqueous sodium hydroxide, brine) and evaporated. Chromatography, with hexane:ethyl acetate as the eluent (4:1 then 2:1) yielded the title compound as a white solid (1.25 g); mp: 79-80° C.; NMR (250 MHz): 1.61 (s,3), 7.69 (m,3), 7.82 (m,2), 7.94 (d,1, J=9), 7.98 (m,2), 8.52 (s,1), 9.93 (s,1); MS: m/z=408(M+1). Analysis for C16H13ClF3NO4S: Calculated: C, 47.11; H, 3.19; N, 3.44; Found: C, 47.10; H, 3.28; N, 3.38.

Workup

  1. stirringwas stirred for 48 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate extracts were washed (aqueous sodium hydroxide, brine)
  4. customevaporated

Sources & evidence

ORD record
ord-1fc9cc796c6a462693bd866eb3c48cc1
Source dataset
uspto-grants-1999_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05900432

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes