Triphenylphosphine → Benzenesulfonamide, N-[(4S,6S)-5,6-dihydro-6-methyl-7,7-dioxido-4H-thieno[2,3-b]thiopyran-4-yl]-N-ethyl-2-nitro-

HRID 1176721Notes

Reaction equation

HRID 1176721 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C@H:21]1[CH2:26][C@@H:25]([CH3:27])[S:24](=[O:29])(=[O:28])[C:23]2[S:30][CH:31]=[CH:32][C:22]1=2.[CH2:33]([NH:35][S:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N+:45]([O-:47])=[O:46])(=[O:38])=[O:37])[CH3:34]>>[CH2:33]([N:35]([C@H:21]1[CH2:26][C@H:25]([CH3:27])[S:24](=[O:29])(=[O:28])[C:23]2[S:30][CH:31]=[CH:32][C:22]1=2)[S:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[N+:45]([O-:47])=[O:46])(=[O:37])=[O:38])[CH3:34]

Participants

4

Reactant 3

HCID 11776TriphenylphosphineHCID 744706N-ethyl-2-nitrobenzenesulfonamideHCID 15647030HCID 15647030, compound

Product 1

HCID 11683414Benzenesulfonamide, N-[(4S,6S)-5,6-dihydro-6-methyl-7,7-dioxido-4H-thieno[2,3-b]thiopyran-4-yl]-N-ethyl-2-nitro-Yield 81.8%

Conditions

Temperature
-30 °C

Procedure

triphenylphosphine (6.8 g); cis-4-hydroxy-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran-7,7-dioxide (5 g) and N-ethyl-2-nitrobenzenesulfonamide (5.54 g) are mixed under nitrogen atmosphere. The mixture is cooled at −30° C. and diisopropyl azadicarboxylate (4.8 mL) is added. It is stirred until completing the transformation. It is filtered, washed and dried. The isolated raw product is column-purified to give 8.07 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.

Workup

  1. additiondiisopropyl azadicarboxylate (4.8 mL) is added
  2. filtrationIt is filtered
  3. washwashed
  4. customdried
  5. customThe isolated raw product
  6. customis column-purified

Sources & evidence

ORD record
ord-030b27f0b0964573b5bd763d210fee16
Source dataset
uspto-grants-2010_11
Patent number
US07842821B2

Reaction notes

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