1-Bromo-2-Chloroethane → HCID 28917003, compound

HRID 2364261Notes

Reaction equation

HRID 2364261 reaction equation
[H-].[Na+].[S:3]1(=[O:10])(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:12][CH2:13][Cl:14]>CN(C)C=O>[Cl:14][CH2:13][CH2:12][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][S:3]1(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 3035081,4-Butanesultam

Product 1

HCID 28917003HCID 28917003, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cold (0° C.) suspension of sodium hydride (823 mg, 60% in oil, 0.0206 mol) in N,N-dimethylformamide (20 mL) was added a solution of tetrahydro-2H-1,2-thiazine 1,1-dioxide (2.53 g, 0.0187 mol) in N,N-dimethylformamide (30 mL). The resulting mixture was stirred at room temperature 1 hour. 1-Bromo-2-chloroethane was added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, then chromatographed on silica gel (30 to 70%, ethyl acetate in hexanes). The resulting residue was triturated with ether and the solids were filtered off. The filtrate was concentrated to give 2-(2-chloroethyl)tetrahydro-2H-1,2-thiazine 1,1-dioxide, which was partially contaminated with starting material, and was taken on to the next step. 1H NMR (400 MHz, CDCl3) δ 3.60 (t, J=6.6 Hz, 2 H), 3.47-3.42 (m, 4 H), 3.01 (t, J=6.0 Hz, 2 H), 2.18 (m, 2 H), 1.66 (m, 2 H).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customchromatographed on silica gel (30 to 70%, ethyl acetate in hexanes)
  4. customThe resulting residue was triturated with ether
  5. filtrationthe solids were filtered off
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0b49019276134071beceea89446dd798
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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