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

HRID 544749Notes

Reaction equation

HRID 544749 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-ecb85c68df1b4eb9a34bd7c29ea0387b
Source dataset
uspto-grants-1984_05
Patent number
US04451660

Reaction notes

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