Triethylamine → HCID 53968847, compound

HRID 1153722Notes

Reaction equation

HRID 1153722 reaction equation
[C:1]1([CH2:7][S:8](Cl)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([CH:15]=[C:16]1[NH:21][CH2:20][CH2:19][CH2:18][S:17]1)([O-:14])=[O:13].C(N(CC)CC)C>O1CCCC1>[C:1]1([CH2:7][S:8]([N:21]2[CH2:20][CH2:19][CH2:18][S:17][C:16]2=[CH:15][N+:12]([O-:14])=[O:13])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazineHCID 74740Phenylmethanesulfonyl chloride2×

Product 1

HCID 53968847HCID 53968847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

A solution of 2.29 g of phenylmethanesulfonyl chloride in 20 ml of tetrahydrofuran was added drop-by-drop to a stirred slurry of 1.6 g of 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine and 2.02 g of triethylamine in 10 ml of dry tetrahydrofuran at -50° C. The resulting mixture was stirred at -50° C. for 1 hour, 1.0 g of phenylmethanesulfonyl chloride was added, and the mixture was stirred for a further hour. The mixture was partitioned between methylene chloride and water. The organic phase was separated, washed with water and brine, dried (MgSO4) and stripped of solvent. The residue was flash chromatographed over silica gel, using methylene chloride as eluent, to give N-(phenylmethylsulfonyl)-2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (5A), as a pale yellow solid, m.p.: 140°-141° C.

Workup

  1. stirringthe mixture was stirred for a further hour
  2. customThe mixture was partitioned between methylene chloride and water
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customchromatographed over silica gel

Sources & evidence

ORD record
ord-8dcd603fe8c5480e983655a1ab1b29e0
Source dataset
uspto-grants-1984_12
Patent number
US04486427

Reaction notes

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