Hydrochloric Acid → HCID 20375544, compound

HRID 1448789Notes

Reaction equation

HRID 1448789 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].[Br: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]([Br:14])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 756094-Bromophenyl isocyanateHCID 16638702HCID 16638702, compound

Product 1

HCID 20375544HCID 20375544, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4 g (18.4 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 24 hours with 3.6 g (18.4 mmol) of p-bromophenylisocyanate and 1.86 g (18.4 mmol) of triethylamine in 40 ml of absolute dimethylsulfoxide. Thereafter, the mixture is poured into 150 ml of 2-N hydrochloric acid and 100 g of ice and stirred for 20 minutes. The separated precipitate is filtered off under suction and washed neutral with water. The precipitate is taken up in 500 ml of methylene chloride, the turbid solution is dried over sodium sulfate, stirred with 1 g of active carbon and filtered. The filtrate is extracted with four 250 ml portions of semi-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 separated product is extracted with three 300 ml portions of methylene chloride. The combined organic phases are dried over sodium sulfate and evaporated. The residual oil is covered with 5 ml of ethanol, the product separating out after standing for several days. The crystals are filtered off under suction, digested with a small amount of ethanol and dried. There is obtained 3-hydroxy-2-methyl-4-(4-bromophenylcarbamoyl)-2H-thieno[3,4-e]-1,2-thiazine 1,1-dioxide of melting point 138°-140° C.

Workup

  1. filtrationThe separated precipitate is filtered off under suction
  2. washwashed neutral with water
  3. dry with materialthe turbid solution is dried over sodium sulfate
  4. stirringstirred with 1 g of active carbon
  5. filtrationfiltered
  6. extractionThe filtrate is extracted with four 250 ml portions of semi-saturated sodium carbonate solution
  7. extractioneach of the aqueous phases being re-extracted with a small amount of methylene chloride
  8. extractionThe separated product is extracted with three 300 ml portions of methylene chloride
  9. dry with materialThe combined organic phases are dried over sodium sulfate
  10. customevaporated
  11. customthe product separating out
  12. waitafter standing for several days
  13. filtrationThe crystals are filtered off under suction
  14. customdried

Sources & evidence

ORD record
ord-8b6e5e505c1343faa0dc0b8dd4712f9f
Source dataset
uspto-grants-1980_02
Patent number
US04187303

Reaction notes

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