1,3-Dibromopropane → HCID 59700565, compound

HRID 901833Notes

Reaction equation

HRID 901833 reaction equation
[S:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.[Br:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C(OCC)(=O)C>[S:1]1[CH2:6][CH2:5][N:4]([CH2:14][CH2:13][CH2:12][Br:11])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 10340Sodium CarbonateHCID 1510642,3-Dihydro-1,4-benzothiazine

Product 1

HCID 59700565HCID 59700565, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3,4-dihydro-2H-benzo[b][1,4]thiazine (2.0 g, 1.0 eq, 13.24 mmol), 1,3-dibromopropane (14 ml, 10 eq, 132.4 mmol) and anhydrous Na2CO3 (4.21 g, 3.0 eq, 39.7 mmol) in dry DMF (130 ml) was heated at 70° C. for 16 h. The reaction mixture was diluted with ethyl acetate (200 ml) and washed with water and brine. The organic layer was dried (Na2SO4), condensed, and the residue was chromatographed using ethyl acetate and hexanes to obtain the title compound as yellow oil (2.13 g, 59% yield).

Workup

  1. washwashed with water and brine
  2. customThe organic layer was dried
  3. custom(Na2SO4), condensed
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-1f6eea739037431d858d4bbee5c29d3e
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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