Water → HCID 57448205, compound

HRID 1667609Notes

Reaction equation

HRID 1667609 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:13][CH:14]([SH:16])[CH3:15].C(N(CC)CC)C.O>CN(C=O)C>[CH:14]([S:16][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[C:4]#[N:5])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 63642-PropanethiolHCID 8471TriethylamineHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 57448205HCID 57448205, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzonitrile (2.5 g, 15.6 mmol) in DMF (50 mL) were added 2-propane thiol (1.74 mL, 18.6 mmol) and triethylamine (4.8 mL, 34.4 mmol). After stirring at ambient temperature for 1 h, the reaction mixture was poured into water (250 mL) and extracted with methylene chloride (3×50 mL). The organic layer was washed with water (2×) and brine, then dried over MgSO4 and concentrated to yield 2.98 g (86%) of 15A as a yellow oil which solidified upon standing.

Workup

  1. extractionextracted with methylene chloride (3×50 mL)
  2. washThe organic layer was washed with water (2×) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1d8d1a471c3944a5907b62802ba8ee51
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

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