Hydrochloric Acid → HCID 20375541, compound

HRID 1448781Notes

Reaction equation

HRID 1448781 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH2:6][C:5]2[CH:9]=[CH:10][S: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[S:11][CH:10]=[CH:9][C:5]=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 20375549HCID 20375549, compound

Product 1

HCID 20375541HCID 20375541, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.8 g (8.3 mmol) of 3,4-dihydro-2-methyl-3-oxo-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide are stirred for 24 hours at room temperature under nitrogen with 1.6 g (8.3 mmol) of p-bromophenylisocyanate and 0.84 g (8.3 mmol) of triethylamine in 20 ml of absolute dimethyl sulfoxide. Thereafter, the mixture is poured into 50 ml of 2-N hydrochloric acid and 20 g of ice. The separated precipitate is filtered off under suction and washed neutral with water. The filter residue is taken up in 200 ml of methylene chloride, dried over sodium sulfate, stirred with 1 g of active carbon and filtered. The filtrate is extracted with four 100 ml portions of semi-saturated sodium carbonate solution, each of the organic 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 100 ml portions of methylene chloride. The combined organic phases are dried over sodium sulfate and evaporated, whereby the product crystallizes out. For purification, the product is recrystallized from ca 30 ml of methanol to give 3-hydroxy-2-methyl-4-(4-bromophenylcarbamoyl)-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide of melting point 197°-199° C.

Workup

  1. filtrationThe separated precipitate is filtered off under suction
  2. washwashed neutral with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. extractionThe filtrate is extracted with four 100 ml portions of semi-saturated sodium carbonate solution
  6. extractioneach of the organic phases being re-extracted with a small amount of methylene chloride
  7. extractionThe separated product is extracted with three 100 ml portions of methylene chloride
  8. dry with materialThe combined organic phases are dried over sodium sulfate
  9. customevaporated
  10. customwhereby the product crystallizes out
  11. customFor purification
  12. customthe product is recrystallized from ca 30 ml of methanol

Sources & evidence

ORD record
ord-9218a625d27b48aab8df65adf22f6022
Source dataset
uspto-grants-1980_02
Patent number
US04187303

Reaction notes

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