Sulfuric Acid → HCID 86601163, compound

HRID 1173312Notes

Reaction equation

HRID 1173312 reaction equation
[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1)=[C:3]([Cl:5])[Cl:4].O[CH2:14][NH:15][C:16](=[O:19])[CH2:17][Cl:18].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Cl:18][CH2:17][C:16]([NH:15][CH2:14][C:9]1[CH:10]=[CH:11][C:6]([C:2]([Cl:1])=[C:3]([Cl:4])[Cl:5])=[CH:7][C:8]=1[OH:12])=[O:19]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 62466N-Methylol-alpha-chloroacetamideHCID 516892Sodium BicarbonateHCID 86601162HCID 86601162, compound

Product 1

HCID 86601163HCID 86601163, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.02 g (9.0 mmol) of the product of Step D and 1.10 g (9.0 mmol) of N-hydroxymethyl-2-chloroacetamide was added in portions to a vigorously stirred solution of 9.0 mL acetic acid and 1.0 mL (98%) sulfuric acid at 0-10° C. The reaction mixture was allowed to warm to room temperature over several hours, and stirring was maintained for a total of 2 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 a gradient of 10-30% EtOAc in hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. temperaturewas maintained for a total of 2 days
  2. extractionextracted into CH2Cl2
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with a gradient of 10-30% EtOAc in hexane
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-36560f67ed404a7fac5d56dfeb74e23e
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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