Sodium methanethiolate → HCID 70976591, compound

HRID 1405178Notes

Reaction equation

HRID 1405178 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([F:15])[CH:7]=1>C(O)C.[Cl-].[Na+].O>[F:15][C:8]1[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:6]([CH2:5][S:2][CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 569243861-(Chloromethyl)-3-fluoro-5-nitrobenzene

Product 1

HCID 70976591HCID 70976591, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium methanethiolate (1.22 g; 17.4 mmol) was added in three portions to a stirred solution of 1-(chloromethyl)-3-fluoro-5-nitrobenzene (3.00 g; 15.8 mmol, HE Chemical) in ethanol (33 ml) at 0° C. The ice bath was removed and the batch was stirred at room temperature for 18 hours. Further sodium methanethiolate (0.33 g; 4.7 mmol) was added and the batch was stirred for 5 additional hours at room temperature. The batch was diluted with brine and extracted with ethyl acetate (2×). The combined organic phases were washed with water, dried (sodium sulfate), filtered and concentrated to give the desired product (3.4 g) that was used without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ=8.00 (m, 1H), 7.81 (m, 1H), 7.42 (m, 1H), 3.74 (s, 2H), 2.02 (s, 3H).

Workup

  1. customThe ice bath was removed
  2. stirringthe batch was stirred for 5 additional hours at room temperature
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-044237ca63384469b8f8bc7e3add210e
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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