Triethylamine → HCID 53647106, compound

HRID 1248627Notes

Reaction equation

HRID 1248627 reaction equation
C(N(CC)CC)C.[N+:8]([CH:11]=[C:12]1[NH:17][CH2:16][CH2:15][CH2:14][S:13]1)([O-:10])=[O:9].[Cl:18][CH2:19][CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[Cl:18][CH2:19][CH2:20][CH2:21][S:22]([N:17]1[CH2:16][CH2:15][CH2:14][S:13][C:12]1=[CH:11][N+:8]([O-:10])=[O:9])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 428532-nitromethylenetetrahydro-2H-1,3-thiazine

Product 1

HCID 53647106HCID 53647106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 ml of triethylamine was added to a solution of 4.8 g of 2-(nitromethylene)-tetrahydro-2H-1,3-thiazine in 100 ml of dichloromethane at -15° C. under nitrogen. Then a solution of 5.9 g of 3-chloropropylsulfonyl chloride in 50 ml of dichloromethane was added drop-by-drop over 25 minutes. The resulting mixture was allowed to warm to room temperature, stirred for one hour and washed with 2% hydrochloric acid solution. The organic phase was separated, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with methanol to give N-(3-chloropropylsulfonyl)-2-(nitromethylene)-tetrahydro-2H-1,3-thiazine (1A), as a solid, m.p.: 99°-99° C.

Workup

  1. washwashed with 2% hydrochloric acid solution
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-8d7eb216fce8425e8d16b007346d3d2a
Source dataset
uspto-grants-1985_06
Patent number
US04525474

Reaction notes

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