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Tributylphosphine → trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide

HRID 1176722
Notes
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Reaction equation

HRID 1176722 reaction equation
O[C@H:2]1[CH2:7][C@@H:6]([CH3:8])[S:5](=[O:10])(=[O:9])[C:4]2[S:11][CH:12]=[CH:13][C:3]1=2.C(P(CCCC)CCCC)CCC.[CH2:27]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:32])=[O:31])[CH3:28]>>[CH2:27]([N:29]([C@H:2]1[CH2:7][C@H:6]([CH3:8])[S:5](=[O:10])(=[O:9])[C:4]2[S:11][CH:12]=[CH:13][C:3]1=2)[S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[N+:39]([O-:41])=[O:40])(=[O:31])=[O:32])[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 13831Tributylphosphine2×HCID 744706N-ethyl-2-nitrobenzene-1-sulfonamideHCID 15647030HCID 15647030, compound

Product 1

HCID 11683414trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxideYield 20.4%

Conditions

Temperature
-30 °C

Procedure

cis-4-hydroxy-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide (5 g), tributylphosphine (6.6 mL) and N-ethyl-2-nitrobenzenesulfonamide (6.17 g) are mixed under nitrogen atmosphere. It is cooled at −20/−30° C. Diisopropyl azadicarboxylate (4.8 mL) is added, maintaining the temperature. It is maintained under stirring, maintaining the temperature, for 4 hours. Tributylphosphine (1.5 mL) and diisopropyl azadicarboxylate (1.5 mL) are added. It is left to reach 20-25° C. and maintained for 30 minutes. It is cooled at 0-5° C.; it is filtered, washed with cold toluene and dried. After purifying by resuspension in methanol, 2.01 g of trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide are obtained.

Workup

  1. additionDiisopropyl azadicarboxylate (4.8 mL) is added
  2. temperaturemaintaining the temperature
  3. temperatureIt is maintained
  4. temperaturemaintaining the temperature
  5. waitIt is left
  6. customto reach 20-25° C.
  7. temperaturemaintained for 30 minutes
  8. temperatureIt is cooled at 0-5° C.
  9. filtrationit is filtered
  10. washwashed with cold toluene
  11. customdried
  12. customAfter purifying by resuspension in methanol

Sources & evidence

ORD record
ord-9489c600b6064b9081ddcbec68ce2d18
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842821B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes