HCID 19907223, compound → HCID 10040931, compound

HRID 2371414Notes

Reaction equation

HRID 2371414 reaction equation
[C:1]([CH:4](CC(O)=O)[CH2:5][S:6][C:7]1[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][C:8]=1[N+:16]([O-])=O)([OH:3])=[O:2].C(Cl)(Cl)Cl.[CH3:27][OH:28]>O.C(O)(=O)C.[Cl-].[Cl-].[Cl-].[Ti+3]>[C:1]([CH2:4][CH:5]1[S:6][C:7]2[S:11][C:10]([S:12](=[O:13])(=[O:14])[NH2:15])=[CH:9][C:8]=2[NH:16][C:27]1=[O:28])([OH:3])=[O:2]

Participants

6

Reactant 2

HCID 19907223HCID 19907223, compoundHCID 21584188Chloroform methanol

Product 1

HCID 10040931HCID 10040931, compound

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Titanium trichloride (256 ml, 15 wt % in 20-30 wt % HCl) was added in a steady stream to a stirred suspension of 5-(2,3-dicarboxypropylthio)-4-nitrothiophene-2-sulfonamide (21.8 g, 61.0 mmol) in water (128 ml) and acetic acid (128 ml). This mixture was stirred at ambient temperature for 18 hours and the yellow solid that precipitated was collected by filtration, washed with water and dried to yield 17.6 g. Chromatography over silica gel using chloroform/methanol/conc. aqueous ammonia (60:30:10; v/v/v) followed by recrystallization from water gave 3-carboxymethyl-2,3-dihydro-2-oxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazine, mp 240° C.

Workup

  1. filtrationthe yellow solid that precipitated was collected by filtration
  2. washwashed with water
  3. customdried
  4. customto yield 17.6 g
  5. customaqueous ammonia (60:30:10; v/v/v) followed by recrystallization from water

Sources & evidence

ORD record
ord-5eed1143a4b049e4873ec0be50a56f3f
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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