Chloroacetone → HCID 71076691, compound

HRID 1774480Notes

Reaction equation

HRID 1774480 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl[CH2:19][C:20](=[O:22])[CH3:21]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:19][C:20](=[O:22])[CH3:21])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 81531DiisopropylethylamineHCID 226073863-Pyridinethiol, 5-bromo-

Product 1

HCID 71076691HCID 71076691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-pyridine-3-thiol (0.880 g, 4.63 mmol) in THF (100 mL) was cooled to 0° C. and Hünig's base (2.4 mL, 13.89 mmol) was added. Chloroacetone (0.371 mL, 4.63 mmol) was added and the ice bath was removed. After 15 minutes the reaction mixture was concentrated, diluted with EtOAc, and washed with H2O/brine. After drying over MgSO4 the mixture was concentrated and purified on silica gel (0-50% EtOAc in hexanes) to give the title compound.

Workup

  1. customthe ice bath was removed
  2. concentrationAfter 15 minutes the reaction mixture was concentrated
  3. additiondiluted with EtOAc
  4. washwashed with H2O/brine
  5. dry with materialAfter drying over MgSO4 the mixture
  6. concentrationwas concentrated
  7. custompurified on silica gel (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d48a9ae2ec5740beaceb769b5a4863ff
Source dataset
uspto-grants-2016_02
Patent number
US09260416B2

Reaction notes

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