Methanol → HCID 86745510, compound

HRID 2371420Notes

Reaction equation

HRID 2371420 reaction equation
[O:1]=[C:2]1[CH:7]([CH2:8][C:9]([OH:11])=[O:10])[S:6](=[O:13])(=[O:12])[C:5]2[S:14][C:15]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:16][C:4]=2[NH:3]1.S(=O)(=O)(O)O.[CH3:26]O>>[O:1]=[C:2]1[CH:7]([CH2:8][C:9]([O:11][CH3:26])=[O:10])[S:6](=[O:13])(=[O:12])[C:5]2[S:14][C:15]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:16][C:4]=2[NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10359893HCID 10359893, compound

Product 1

HCID 86745510HCID 86745510, compound

Procedure

A mixture of (2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetic acid (5 g) and concentrated sulfuric acid (3 ml) in methanol (50 ml) was heated to reflux for 5 hours. The solvent was removed and the residue was treated with ice cold water. The resulting solid was collected, rinsed with additional cold water and dried at 50° C. to yield 4.05 g. Recrystallization from water gave methyl (2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetate, mp 223°-225° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. customThe solvent was removed
  4. additionthe residue was treated with ice cold water
  5. customThe resulting solid was collected
  6. washrinsed with additional cold water
  7. customdried at 50° C.
  8. customto yield 4.05 g
  9. customRecrystallization from water

Sources & evidence

ORD record
ord-584c26b8131540b495e64e6260ac1c82
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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