Water → 2-Methyl-3-methylthiomethyl-7-nitrobenzo[b]furan

HRID 342428Notes

Reaction equation

HRID 342428 reaction equation
Cl[CH2:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8].[CH3:16][S-:17].[Na+].O>CN(C)C=O>[CH3:8][C:7]1[O:6][C:5]2[C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=[CH:12][C:4]=2[C:3]=1[CH2:2][S:17][CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 701999963-Chloromethyl-2-methyl-7-nitrobenzo[b]furan

Product 1

HCID 675582772-Methyl-3-methylthiomethyl-7-nitrobenzo[b]furanYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-chloromethyl-2-methyl-7-nitrobenzo[b]furan (200 mg) and sodium thiomethoxide (68 mg) in N,N-dimethylformamide (2 ml) was stirred at ambient temperature for 2 hours. The reaction mixture was poured into cold water and the separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 2-methyl-3-methylthiomethyl-7-nitrobenzo[b]furan (144 mg).

Workup

  1. extractionthe separated oil was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f353448f02d74242a78a6cc629a40c9e
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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