Hydrochloric Acid → HCID 20375535, compound

HRID 1448794Notes

Reaction equation

HRID 1448794 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][C:5]2=[CH:9][S:10][CH:11]=[C:4]2[S:3]1(=[O:13])=[O:12].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1.C(N(CC)CC)C.Cl>CS(C)=O>[OH:8][C:7]1[N:2]([CH3:1])[S:3](=[O:13])(=[O:12])[C:4]2[C:5](=[CH:9][S:10][CH:11]=2)[C:6]=1[C:22](=[O:23])[NH:21][C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 16638702HCID 16638702, compound

Product 1

HCID 20375535HCID 20375535, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1 g (4.6 mmol) of 3,4-dihydro-2-methyl-3-oxo-2H-thieno[3,4-e]-1,2-thiazine 1,1-dioxide are stirred at room temperature under nitrogen for 3 hours with 0.71 g (4.6 mmol) of p-chlorophenylisocyanate and 0.47 g (4.6 mmol) of triethylamine in 10 ml of absolute dimethylsulfoxide. Thereafter, the mixture is poured into 40 ml of 2-N hydrochloric acid and 25 g of ice and stirred for 20 minutes. The separated precipitate is filtered off under suction and washed neutral with water. The precipitate is dissolved in 200 ml of methylene chloride, the turbid solution is dried over sodium sulfate, stirred with 0.3 g of active carbon and filtered. The filtrate is extracted with five 100 ml portions of saturated sodium carbonate solution, each of the aqueous phases being re-extracted with a small amount of methylene chloride. The combined aqueous phases are acidified to pH 1 with concentrated hydrochloric acid. The precipitated product is extracted with two 150 ml portions of methylene chloride. The combined organic phases are dried over sodium sulfate. The solvent is distilled off, whereby the product crystallizes out. For purification, the product is recrystallized from ca 30 ml of methanol. There is obtained 3-hydroxy-2-methyl-4-(4-chlorophenylcarbamoyl)-2H-thieno[3,4-e]-1,2-thiazine 1,1-dioxide of melting point 154°-156° C.

Workup

  1. filtrationThe separated precipitate is filtered off under suction
  2. washwashed neutral with water
  3. dissolutionThe precipitate is dissolved in 200 ml of methylene chloride
  4. dry with materialthe turbid solution is dried over sodium sulfate
  5. stirringstirred with 0.3 g of active carbon
  6. filtrationfiltered
  7. extractionThe filtrate is extracted with five 100 ml portions of saturated sodium carbonate solution
  8. extractioneach of the aqueous phases being re-extracted with a small amount of methylene chloride
  9. extractionThe precipitated product is extracted with two 150 ml portions of methylene chloride
  10. dry with materialThe combined organic phases are dried over sodium sulfate
  11. distillationThe solvent is distilled off
  12. customwhereby the product crystallizes out
  13. customFor purification
  14. customthe product is recrystallized from ca 30 ml of methanol

Sources & evidence

ORD record
ord-e77a2e214c3d40389645893b7c47f03d
Source dataset
uspto-grants-1980_02
Patent number
US04187303

Reaction notes

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