Hydrochloric Acid → N-(Phenylsulfonyl)-tetrahydro-2-nitromethylene-2H-1,3-thiazine

HRID 364863Notes

Reaction equation

HRID 364863 reaction equation
CC(C)([O-])C.[K+].[SH:7][CH2:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13].Cl[C:22](Cl)=[CH:23][N+:24]([O-:26])=[O:25].Cl.[Cl-].[Na+]>C(O)(C)(C)C>[C:15]1([S:12]([N:11]2[CH2:10][CH2:9][CH2:8][S:7][C:22]2=[CH:23][N+:24]([O-:26])=[O:25])(=[O:14])=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 122195711,1-Dichloro-2-nitroetheneHCID 20238482N-(3-Mercaptopropyl)benzenesulfonamideHCID 23665647Potassium tert-butoxide

Product 1

HCID 53713608N-(Phenylsulfonyl)-tetrahydro-2-nitromethylene-2H-1,3-thiazine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

0.22 g of potassium t-butoxide was added drop-by-drop over 10 minutes to a solution of 0.23 g of 3 in 5 ml of t-butanol, under nitrogen. The resulting mixture was added drop-by-drop over 20 minutes to 0.30 g of 13A. After 20 minutes at room temperature, the mixture was poured into 2% hydrochloric acid saturated with sodium chloride, the resulting mixture was extracted with methylene chloride, the solvent was evaporated from the extract and the residue was purified over silica gel, using methylene chloride as eluent, to give 25, m.p.: 106°-107° C.

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride
  2. customthe solvent was evaporated from the
  3. extractionextract
  4. customthe residue was purified over silica gel

Sources & evidence

ORD record
ord-6059c51c7870432290af348debf650f2
Source dataset
uspto-grants-1986_08
Patent number
US04606862

Reaction notes

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