Methanesulfonyl chloride → HCID 67215005, compound

HRID 2421034Notes

Reaction equation

HRID 2421034 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[N:4][C:3]=1[C:16]([O:18]CC)=[O:17].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:2]([NH:1][S:22]([CH3:21])(=[O:24])=[O:23])=[C:3]([C:16]([OH:18])=[O:17])[N:4]=[N:5]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chloride3×HCID 67214764HCID 67214764, compound

Product 1

HCID 67215005HCID 67215005, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 5-amino-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate (0.85 g) and methane sulphonyl chloride (0.72 mL) were stirred in pyridine (20 mL) for 4 d. Further methane sulphonyl chloride (0.72 mL) was added and stirring continued for 24 h. Further methane sulphonyl chloride (0.5 mL) was added and stirring continued for 24 h. The mixture was concentrated in vacuo. The residue was suspended in dilute hydrochloric acid and extracted with ethyl acetate. The extracts were washed with dilute hydrochloric acid and water then evaporated. The residue was taken up in ethanol (70 mL) and 2 M sodium hydroxide solution (70 mL) and stirred for 18 h. The mixture was concentrated to about half volume and acidified with dilute hydrochloric acid. The mixture was extracted with ethyl acetate and the extracts were washed with water and brine, then dried and evaporated to leave a white solid (0.90 g).

Workup

  1. stirringstirring
  2. waitcontinued for 24 h
  3. concentrationThe mixture was concentrated in vacuo
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with dilute hydrochloric acid and water
  6. customthen evaporated
  7. stirring2 M sodium hydroxide solution (70 mL) and stirred for 18 h
  8. concentrationThe mixture was concentrated to about half volume
  9. extractionThe mixture was extracted with ethyl acetate
  10. washthe extracts were washed with water and brine
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-fe8058fbaa38499caba778cee32698b4
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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