Water → HCID 57751034, compound

HRID 2283367Notes

Reaction equation

HRID 2283367 reaction equation
Cl[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8].C(N(CC)C(C)C)(C)C.[CH2:19]([SH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CS(C)=O.C(OCC)(=O)C>[CH2:19]([S:26][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[N+:7]([O-:9])=[O:8])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 2201862-Chloro-3-nitrothiophene

Product 1

HCID 57751034HCID 57751034, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-3-nitrothiophene (1.00 g, 6.11 mmol), N,N-diisopropylethylamine (2.1 mL, 12.22 mmol) and benzyl mercaptan (0.8 mL, 6.72 mmol) in dimethyl sulfoxide (5 mL) was placed in a sealed tube. The reaction mixture was heated at 80° C. for 1 hour, cooled to room temperature and water (10 mL) was added. The mixture was diluted with ethyl acetate (50 mL) and the organic phase was washed with brine, dried over magnesium sulfate, concentrated in vacuo and dried in vacuo to give 97% yield of the title compound.

Workup

  1. customwas placed in a sealed tube
  2. temperaturecooled to room temperature
  3. washthe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customdried in vacuo

Sources & evidence

ORD record
ord-31b6f24c28ed49519c74c8ccd3414d60
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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