HCID 2653166, compound → HCID 21878237, compound

HRID 723821Notes

Reaction equation

HRID 723821 reaction equation
Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[S-:18][CH2:19][CH3:20].[Na+]>O1CCCC1>[CH2:19]([S:18][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2653166HCID 2653166, compoundHCID 4459711Sodium ethanethiolate2×

Product 1

HCID 21878237HCID 21878237, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a round-bottomed flask equipped with a condenser was placed 6-chloro-N-(4-fluoro-phenyl)-nicotinamide (0.20 g, 0.80 mmol), tetrahydrofuran (6 mL), and sodium thioethoxide (0.10 g, 1.2 mmol). The mixture was heated to reflux for 4 h at which time additional sodium thioethoxide (0.10 g, 1.2 mmol) was added and stirred for 2 additional hours. The reaction mixture was then cooled and poured into ice water and the solids isolated by vacuum filtration to provide 0.15 g (68%) of the product as a white solid. MS (EI) m/z 275.2 (M−H)−.

Workup

  1. customInto a round-bottomed flask equipped with a condenser
  2. temperatureThe mixture was heated
  3. additionwas added
  4. temperatureThe reaction mixture was then cooled
  5. customthe solids isolated by vacuum filtration

Sources & evidence

ORD record
ord-0f07547570e141c89f36e18795d8847b
Source dataset
uspto-grants-2006_11
Patent number
US07141590B2

Reaction notes

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