Acetic Acid → HCID 66883117, compound

HRID 220211Notes

Reaction equation

HRID 220211 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=O.[N+:14]([CH2:17][CH3:18])([O-:16])=[O:15].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(OC(=O)C)C>[Cl:1][C:2]1[C:3]2[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:4]=2[S:5][C:6]=1/[CH:7]=[CH:18]/[CH2:17][N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 73554822HCID 73554822, compound

Product 1

HCID 66883117HCID 66883117, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In a sulfonation flask, a mixture containing 6.93 g (0.03 mol) 3,5-dichlorobenzo[b]thio-phene-2-carbaldehyde, 18 g (0.24 mol) nitroethane, 5.8 g (0.075 mol) ammoniumacetate and 60 ml acetic acid is heated at 90° C. for 6 hours. After cooling ethylacetate is added and the organic phase washed three times with water. The organic phase is dried over sodium sulphate and after filration the organic solvent is distilled off in a water jet vacuum. The residue is purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:5). After chromatography further purification via crystallisation from ethylacetate could be achieved. Yield: 4 g (47% of theory). M.p. 143°-146° C.

Workup

  1. additionis added
  2. washthe organic phase washed three times with water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. distillationafter filration the organic solvent is distilled off in a water jet vacuum
  5. customThe residue is purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:5)
  6. customAfter chromatography further purification
  7. customvia crystallisation from ethylacetate

Sources & evidence

ORD record
ord-bde03bf043104c0abcf62b1ec8b729c7
Source dataset
uspto-grants-2012_06
Patent number
US08202894B2

Reaction notes

Loading…