Ammonia → HCID 23114853, compound

HRID 2080437Notes

Reaction equation

HRID 2080437 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:12]2[N:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20](O)=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH3:35]>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[C:12]2[N:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([NH2:35])=[O:21])=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 23114614HCID 23114614, compound

Product 1

HCID 23114853HCID 23114853, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

In dichloromethane (6 ml) was dissolved (E)-3-[6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]acrylic acid (370 mg, 0.822 mmol). To the resulting solution were added thionyl chloride (2.00 ml) and N,N-dimethylformamide (one drop). The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated to dryness. The residue thus obtained was dissolved in dichloromethane (6 ml), followed by the addition of aqueous concentrated ammonia (2.00 ml). After stirring at room temperature for 2 hours, the reaction mixture was diluted with dichloromethane. The diluted mixture was washed with water, 0.1N hydrochloric acid and brine, dried over magnesium sulfate, and concentrated. The solid thus obtained was recrystallized from ethanol to give the title compound (250 mg, 0.558 mmol, 68%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe residue thus obtained
  3. stirringAfter stirring at room temperature for 2 hours
  4. washThe diluted mixture was washed with water, 0.1N hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe solid thus obtained
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-38ab79d32e9348a9b0489b3052c41661
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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