Methanethiol → 1-[5-(Methylsulfanyl)-4-nitrothiophen-2-yl]ethan-1-one

HRID 1905949Notes

Reaction equation

HRID 1905949 reaction equation
[CH3:1][SH:2].Cl[C:4]1[S:5][C:6]([C:12](=[O:14])[CH3:13])=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O>C(O)C>[CH3:1][S:2][C:4]1[S:5][C:6]([C:12](=[O:14])[CH3:13])=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 878MethanethiolHCID 962WaterHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

Product 1

HCID 202136841-[5-(Methylsulfanyl)-4-nitrothiophen-2-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Liquid methylmercaptan (4 ml) was added to a solution of 0.82 g of Na in 50 ml of absolute ethanol. The resulting solution was added to a solution of 7.2 g of 2-chloro-3-nitro-5-acetylthiophene in 200 ml of absolute ethanol in 15 minutes at 5° C. After stirring at room temperature for 30 minutes, 100 ml of water was added, after which the precipitate was sucked off and washed successively with water and isopropanol. The precipitate was boiled a moment with 300 ml of carbontetrachloride, cooled down, and sucked off. After drying the title compound was obtained in a yield of 6.4 g; m.p. 191°-193° C.

Workup

  1. washwashed successively with water and isopropanol
  2. temperaturecooled down
  3. dry with materialAfter drying the title compound
  4. customwas obtained in a yield of 6.4 g

Sources & evidence

ORD record
ord-f2f88eeedaa947b58ba2cca4da57948f
Source dataset
uspto-grants-1987_03
Patent number
US04649154

Reaction notes

Loading…