Pyridine → HCID 15005407, compound

HRID 2107682Notes

Reaction equation

HRID 2107682 reaction equation
Br[CH:2]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[C:3](=O)[CH3:4].[C:14]([NH2:17])(=[S:16])[CH3:15].N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([C:2]2[S:16][C:14]([CH3:15])=[N:17][C:3]=2[CH3:4])=[CH:7][CH:8]=1)#[N:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2723949ThioacetamideHCID 15005405HCID 15005405, compound

Product 1

HCID 15005407HCID 15005407, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-(1-bromo-2-oxopropyl)benzonitrile (0.9 g, 3.83 mmol) in toluene (2 ml) was treated with thioacetamide (0.6 g, 8 mmol) followed by pyridine (0.45 ml). The mixture was warmed to 100° C. for 1 hour, then partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4) and evaporated to a yellow oil. Chromatography on silica gel, eluting with 5% ether in dichloromethane, afforded a pale yellow oil which crystallised (0.52 g, 64%), m.p. 108°-110° C.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated to a yellow oil
  4. washChromatography on silica gel, eluting with 5% ether in dichloromethane
  5. customafforded a pale yellow oil which
  6. customcrystallised (0.52 g, 64%), m.p. 108°-110° C.

Sources & evidence

ORD record
ord-872d67d757f94937be4498c43bc822f2
Source dataset
uspto-grants-1990_06
Patent number
US04935430

Reaction notes

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