Lawesson's reagent → HCID 19907226, compound

HRID 2371417Notes

Reaction equation

HRID 2371417 reaction equation
O=[C:2]1[CH2:7][S:6](=[O:9])(=[O:8])[C:5]2[S:10][C:11]([S:13](=[O:16])(=[O:15])[NH2:14])=[CH:12][C:4]=2[NH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:26])=CC=1>C(COC)OC>[O:8]=[S:6]1(=[O:9])[CH2:7][C:2](=[S:26])[NH:3][C:4]2[CH:12]=[C:11]([S:13](=[O:16])(=[O:15])[NH2:14])[S:10][C:5]1=2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10379035HCID 10379035, compound

Product 1

HCID 19907226HCID 19907226, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine (5 g) and Lawesson's reagent (3.8 g) in dimethoxyethane (25 ml) was heated under reflux for seven hours. The solvent was removed under reduced pressure and the residue was chromatographed over silica gel with chloroform/methanol/acetic acid (90:8:2, v/v/v) as the eluent. The fractions containing the desired product were combined and evaporated to dryness to yield 1.4 g. Two recrystallizations from ethyl acetate/hexane gave pure 2,3-dihydro-4,4-dioxo-6-sulfamoyl-2-thiono-1H-thieno[2,3-b][1,4]thiazine, mp 219°-221° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for seven hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was chromatographed over silica gel with chloroform/methanol/acetic acid (90:8:2, v/v/v) as the eluent
  5. additionThe fractions containing the desired product
  6. customevaporated to dryness
  7. customto yield 1.4 g
  8. customTwo recrystallizations from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4c8bb7c200e54fe8b4a70d5d9f535149
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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