Sulfuric Acid → 2-Chloro-N-[2-hydroxy-4,6-bis(trichlorovinyl)benzyl]acetamide

HRID 1173318Notes

Reaction equation

HRID 1173318 reaction equation
[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([OH:17])[CH:9]=[C:10]([C:12]([Cl:16])=[C:13]([Cl:15])[Cl:14])[CH:11]=1)=[C:3]([Cl:5])[Cl:4].O[CH2:19][NH:20][C:21](=[O:24])[CH2:22][Cl:23].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:23][CH2:22][C:21]([NH:20][CH2:19][C:7]1[C:6]([C:2]([Cl:1])=[C:3]([Cl:5])[Cl:4])=[CH:11][C:10]([C:12]([Cl:16])=[C:13]([Cl:14])[Cl:15])=[CH:9][C:8]=1[OH:17])=[O:24]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 62466N-Methylol-alpha-chloroacetamideHCID 516892Sodium BicarbonateHCID 86601168HCID 86601168, compound

Product 1

HCID 866011692-Chloro-N-[2-hydroxy-4,6-bis(trichlorovinyl)benzyl]acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.352 g (1.0 mmol) of the product of Step D and 0.123 g (1.0 mmol) of N-hydroxymethyl-2-chloroacetamide was added in portions to a vigorously stirred solution of 0.9 mL acetic acid and 0.1 mL (98%) sulfuric acid at 0-10° C. The reaction mixture was allowed to warm to room temperature, and stirring was maintained for a total of 4 days. The reaction mixture was poured into ice-water, neutralized with saturated aqueous NaHCO3 solution and extracted into CH2Cl2. The organic extracts were combined, washed with brine, dried Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 5-10% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. temperaturewas maintained for a total of 4 days
  2. extractionextracted into CH2Cl2
  3. washwashed with brine, dried Na2SO4),
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on a silica gel flash chromatography column
  7. washeluted with 5-10% EtOAc in hexane
  8. customEvaporation of the purified fractions
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-1b46ddd11d4d4ca9aafcd4ef260f48d3
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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