Methyl 3-[(methoxycarbonylmethyl)sulfamoyl]-5-trifluoromethyl-thiophene-2-carboxylate → HCID 54677723, compound

HRID 463666Notes

Reaction equation

HRID 463666 reaction equation
[CH3:1][O:2][C:3]([CH2:5][NH:6][S:7]([C:10]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[S:12][C:11]=1[C:19]([O:21]C)=O)(=[O:9])=[O:8])=[O:4]>O1CCCC1>[OH:21][C:19]1[C:11]2[S:12][C:13]([C:15]([F:18])([F:17])[F:16])=[CH:14][C:10]=2[S:7](=[O:9])(=[O:8])[NH:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

3

Reactant 1

HCID 16639955Methyl 3-[(methoxycarbonylmethyl)sulfamoyl]-5-trifluoromethyl-thiophene-2-carboxylate

Product 1

HCID 54677723HCID 54677723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 82.8 g of methyl 3-[(methoxycarbonylmethyl)sulfamoyl]-5-trifluoromethyl-thiopene-2-carboxylate in 1.7 l of absolute tetrahydrofuran is cooled to 3° and treated portionwise at this temperature for 20 minutes with a total of 62.9 g of potassium tert.butylate. Thereafter, the cooling bath is removed, the viscous red paste is stirred at room temperature for 2 hours and then as much tetrahydrofuran as possible is distilled off in vacuo at a maximum temperature of 30°. The powdery residue is taken up in 1.4 l of ice-water, treated with 10 g of active carbon while stirring and suction filtered over siliceous earth. The filtrate is adjusted to pH 2-3 with about 185 ml of 3N hydrochloric acid at a maximum temperature of 5°. The mixture is stirred for 0.5 hour, whereupon the crude product which initially separates in the form of an oil crystallizes (after the addition of ether). The precipitated crude product is removed by filtration under suction, washed neutral with water, dried at 50° overnight in vacuo and recrystallized from methanol. 4-Hydroxy-3-methoxycarbonyl-6-trifluoromethyl-2H-thieno[2,3-e]-1,2-thiazine 1,1-dioxide of melting point 168°-170° is obtained.

Workup

  1. customThereafter, the cooling bath is removed
  2. distillationas much tetrahydrofuran as possible is distilled off in vacuo at a maximum temperature of 30°
  3. additiontreated with 10 g of active carbon
  4. stirringwhile stirring
  5. filtrationsuction filtered over siliceous earth
  6. customis adjusted to pH 2-3 with about 185 ml of 3N hydrochloric acid at a maximum temperature of 5°
  7. stirringThe mixture is stirred for 0.5 hour, whereupon the crude product which
  8. customcrystallizes (
  9. additionafter the addition of ether)
  10. customThe precipitated crude product
  11. customis removed by filtration under suction
  12. washwashed neutral with water
  13. customdried at 50° overnight in vacuo
  14. customrecrystallized from methanol

Sources & evidence

ORD record
ord-8849904b73a64b0c8745a9e773bb5abe
Source dataset
uspto-grants-1985_10
Patent number
US04544655

Reaction notes

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