Acetyl chloride → HCID 22007170, compound

HRID 323791Notes

Reaction equation

HRID 323791 reaction equation
C(Cl)(=O)C.C([O:8][CH:9]([CH2:22][Cl:23])[C:10]1[CH:15]=[C:14]([S:16](=[O:19])(=[O:18])[NH2:17])[CH:13]=[CH:12][C:11]=1[O:20][CH3:21])(=O)C>CO>[Cl:23][CH2:22][CH:9]([C:10]1[CH:15]=[C:14]([S:16](=[O:19])(=[O:18])[NH2:17])[CH:13]=[CH:12][C:11]=1[O:20][CH3:21])[OH:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 22007157HCID 22007157, compound

Product 1

HCID 22007170HCID 22007170, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

61 μl of acetyl chloride are added to 100 ml of methanol and the mixture is stirred for 15 minutes. 1.32 g (−)-α-chloromethyl-2-methoxy-5-sulphamoylbenzyl acetate are then added and the mixture is heated to reflux for 1 hour (degree of conversion of 97% shown by HPLC). The mixture is thereafter evaporated, the residue is then taken up in 100 ml of ethyl acetate and the medium is neutralized with 5 ml of 2% ethyl hydrogen carbonate. The carbonate phase is extracted with 2 times 5 ml of ethyl acetate, the organic phases are then combined, dried and concentrated to 30 ml and cyclohexane is added. After one night at room temperature, the product which has crystallized is filtered off. 1 g of (−)-α-chloromethyl-2-methoxy-5-sulphamoylbenzenemethanol is obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 hour (degree of conversion of 97% shown by HPLC)
  3. customThe mixture is thereafter evaporated
  4. extractionThe carbonate phase is extracted with 2 times 5 ml of ethyl acetate
  5. customdried
  6. concentrationconcentrated to 30 ml and cyclohexane
  7. additionis added
  8. waitAfter one night at room temperature
  9. customthe product which has crystallized
  10. filtrationis filtered off

Sources & evidence

ORD record
ord-0ff9cb45cb4b42c4a18af3a4a1b9b22f
Source dataset
uspto-grants-2001_04
Patent number
US06214882B1

Reaction notes

Loading…