Dimethylformamide → HCID 178518985, compound

HRID 909398Notes

Reaction equation

HRID 909398 reaction equation
O[NH:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[OH:12].CN(C)C=O.S(Cl)([Cl:21])=O>C(Cl)Cl>[Cl:21][CH2:10][C:7]1[CH:8]=[CH:9][C:4]2[C:3]([OH:13])=[N:2][O:12][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57660218HCID 57660218, compound

Product 1

HCID 178518985HCID 178518985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 mL of methylene chloride was suspended 10.0 g of N,2-dihydroxy-4-(hydroxymethyl)benzamide. To this, 0.21 mL of N,N-dimethylformamide was added. This was cooled and 8.36 mL of thionyl chloride was added dropwise under ice-cooling. After 2 hours of stirring under heating reflux, 13 mL of solvent was distilled off under atmospheric pressure. To the reaction mixture was added 13 mL of methylene chloride, 4.64 mL of pyridine was added dropwise at 20-30° C., and the results were stirred for 1 hour at the same temperature. After adding 20 mL of water and 50 mL of acetone, 50 mL of solvent was distilled off under atmospheric pressure, solids were filtered, and 6.45 g of 6-(chloromethyl)-1,2-benzisoxazol-3-ol in the form of a pale yellowish-white solid was obtained.

Workup

  1. temperatureThis was cooled
  2. temperaturecooling
  3. temperatureunder heating
  4. temperaturereflux
  5. distillation13 mL of solvent was distilled off under atmospheric pressure
  6. additionTo the reaction mixture was added 13 mL of methylene chloride, 4.64 mL of pyridine
  7. additionwas added dropwise at 20-30° C.
  8. stirringthe results were stirred for 1 hour at the same temperature
  9. additionAfter adding 20 mL of water and 50 mL of acetone, 50 mL of solvent
  10. distillationwas distilled off under atmospheric pressure, solids
  11. filtrationwere filtered

Sources & evidence

ORD record
ord-d0429b5390784502b59b16c1b629f83f
Source dataset
uspto-grants-2011_09
Patent number
US08017789B2

Reaction notes

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