ethyl N-ethoxycarbonyliminocarbamate → 3,4-Dihydro-3-methyl-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxide

HRID 1768627Notes

Reaction equation

HRID 1768627 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH:14]([CH3:25])[CH2:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[S:21]([NH2:24])(=[O:23])=[O:22]>C1COCC1>[CH3:25][CH:14]1[CH2:15][C:16]2[CH:20]=[CH:19][S:18][C:17]=2[S:21](=[O:23])(=[O:22])[NH:24]1

Participants

4

Reactant 2

HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 229019693-(2-Hydroxypropyl)thiophene-2-sulfonamide

Product 1

HCID 229019703,4-Dihydro-3-methyl-2H-thieno[3,2-e]-1,2-thiazine 1,1-dioxideYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylphosphene (3.6 g, 13.76 mmol) and diethyl azodicarboxylate (2.2 mL, 13.76 mmol) were dissolved in THF (10 mL) and cooled to 0° C. To this was added a solution of the product from Step A (1.9 g, 8.6 mmol) in THF (10 mL) and the mixture was stirred at 0° C. for 3 hr. The solvent was evaporated and the residue dissolved in ethyl acetate (100 mL); this solution was washed with water (2×50 mL) and brine (2×50 mL), dried (MgSO4), and evaporated to a syrup which was purified by column chromatography (silica, 1:2 hexane/ethyl acetate) to give the desired product (995 mg, 57%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (100 mL)
  3. washthis solution was washed with water (2×50 mL) and brine (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated to a syrup which
  6. customwas purified by column chromatography (silica, 1:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bcbbf454c86b4c7292d5d45a6c0918ae
Source dataset
uspto-grants-1995_01
Patent number
US05378703

Reaction notes

Loading…