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Sodium Bicarbonate → N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamide

HRID 1662222
Notes
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Reaction equation

HRID 1662222 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([C:10](=O)[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[C:5]([C:6]#[N:7])=[C:4]([F:20])[CH:3]=1.[CH3:21][C:22]([S:25]([NH2:27])=[O:26])([CH3:24])[CH3:23].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:1][C:2]1[CH:3]=[C:4]([F:20])[C:5]([C:6]#[N:7])=[C:8]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[N:27][S:25]([C:22]([CH3:24])([CH3:23])[CH3:21])=[O:26])[CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 585795244-Chloro-2-fluoro-6-(3-methoxybenzoyl)benzonitrile

Product 1

HCID 76821604N-((5-chloro-2-cyano-3-fluorophenyl)(3-methoxyphenyl)methylene)-2-methylpropane-2-sulfinamideYield 59%

Reagents, catalysts & solvents 3

HCID 76524
Titanium tetraethoxide
Catalyst
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

4-Chloro-2-fluoro-6-(3-methoxybenzoyl)benzonitrile (2.56 g, 8.84 mmol), 2-methyl-2-propanesulfinamide (1.392 g, 11.49 mmol) and titanium(IV) ethoxide (4.62 mL, 22.09 mmol) were dissolved in THF (30 mL) and stirred at 75° C. over weekend. When cooled to rt, the mixture was diluted with DCM (25 mL). Saturated aqueous NaHCO3 (3 mL) was added followed by silica and the mixture concentrated under reduced pressure until a free flowing powder was obtained. Purification on a silica gel column (0-40% EtOAc in heptane as eluent) gave 2.04 g (59% yield) of the title compound.

Workup

  1. temperatureWhen cooled to rt
  2. concentrationthe mixture concentrated under reduced pressure until
  3. customwas obtained
  4. customPurification on a silica gel column (0-40% EtOAc in heptane as eluent)

Sources & evidence

ORD record
ord-751b48230fcf4f98beb5a0f168bc0b32
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08030500B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes