Lawesson's reagent → HCID 59580729, compound

HRID 1470434Notes

Reaction equation

HRID 1470434 reaction equation
[CH3:1][CH:2]([CH2:18][S:19][CH3:20])[C:3]([NH:5][C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:17])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>O1CCOCC1>[CH3:1][CH:2]([CH2:18][S:19][CH3:20])[C:3]([NH:5][C:6]1[S:10][C:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:17])=[S:30]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59580762HCID 59580762, compound

Product 1

HCID 59580729HCID 59580729, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

To a microwave reaction vessel was added 2-methyl-N-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)3-methylsulfanyl-propionamide (0.10 g, 0.32 mmol) in dioxane and Lawesson's reagent (0.19 g, 0.48 mmol). The vessel was capped and heated in a Biotage Initiator microwave reactor for 1 min at 130° C., with external IR-sensor temperature monitoring from the side. The reaction was concentrated to dryness and the crude material was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes) to give the desired product as a yellow semi solid (0.019 g, 18%): 1H NMR (300 MHz, CDCl3) δ 9.9 (m, 1H), 9.2 (d, 1H), 8.65 (d, 1H), 8.4 (m, 1H), 7.4 (m, 1H), 3.15 (m, 1H), 2.9 (m, 2H), 2.5 (s, 3H), 2.2 (s, 3H), 1.5 (d, 3H); ESIMS m/z 324.12 (M+1).

Workup

  1. customTo a microwave reaction vessel
  2. customThe vessel was capped
  3. concentrationThe reaction was concentrated to dryness
  4. customthe crude material was purified by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-21443ae9dddb4ec9ad3fa7e0b8842365
Source dataset
uspto-grants-2015_04
Patent number
US09006446B2

Reaction notes

Loading…