Formic Acid → HCID 20213668, compound

HRID 1905951Notes

Reaction equation

HRID 1905951 reaction equation
C([O-])(O)=O.[Na+].[CH3:6][S:7][C:8]1[S:9][C:10]([CH:16]=O)=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14].[NH2:18]O.Cl.C(O)=O>O>[CH3:6][S:7][C:8]1[S:9][C:10]([C:16]#[N:18])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 20213679HCID 20213679, compound

Product 1

HCID 20213668HCID 20213668, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sodium methyl mercaptide solution was prepared by adding 5 ml of methylmercaptan to 1.75 g of Na in 60 ml of absolute ethanol. While stirring and cooling this solution to below 10° C. it was added to a solution of 17.6 g of 2-bromo-3-nitro-5-formylthiophene in 200 ml of ethanol. After stirring at room temperature for another 2 hours, 200 ml of water were added, after which the formed precipitate was sucked off, washed with water-ethanol mixture (1:1 v/v), and recrystallized from isopropanol. 6.5 g of 2-methylthio-3-nitro-5-formylthiophene of melting point 129°-131° C. were obtained. Then 2.35 g of NaHCO3, 3.1 g of 2-methylthio-3-nitro-5-formylthiophene, and 1.2 g of NH2OH.HCl were added successively to 50 ml of formic acid. The reaction mixture was refluxed for 1 hour, after which, water was added and the formed precipitate was sucked off. After recrystallization from isopropanol the desired 2-methylthio-3-nitro-5-cyanthiophene was obtained in a yield of 2.3 g; melting point 150° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customAfter recrystallization from isopropanol the desired 2-methylthio-3-nitro-5-cyanthiophene
  3. customwas obtained in a yield of 2.3 g

Sources & evidence

ORD record
ord-f36db9db739c4098b6e8df523ffdc186
Source dataset
uspto-grants-1987_03
Patent number
US04649154

Reaction notes

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