1-Bromo-3-chloropropane → HCID 64390252, compound

HRID 1524160Notes

Reaction equation

HRID 1524160 reaction equation
[Br:1][C:2]1[C:3]([SH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][CH2:12][Cl:13].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([S:8][CH2:10][CH2:11][CH2:12][Cl:13])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178527856HCID 178527856, compound

Product 1

HCID 64390252HCID 64390252, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 3-bromopyridine-2-thiol (0.04 g, 0.2 mmol), 1-bromo-3-chloropropane in DMF (0.424 mmol/mL, 2.0 mL), and K2CO3 (60 mg, 0.424 mmol) in DMF (2.0 mL) was stirred at rt for 10 minutes. The reaction mixture was then concentrated to dryness and the resultant residue diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4 and concentrated to dryness to give the title compound (0.05 g, 89% purity). MS (ESI): mass calcd. for C8H9BrClNS, 264.93; m/z found, 265.8 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. additionthe resultant residue diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e1fe139ee9a44780ba3313d4e4fdb488
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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