3-[(4-Chlorophenyl)sulfanyl]pentane-2,4-dione → HCID 22174886, compound

HRID 1897005Notes

Reaction equation

HRID 1897005 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][NH2:14])[N:8]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH:23]([C:27](=O)[CH3:28])[C:24](=O)[CH3:25])=[CH:18][CH:17]=1>C(O)CC>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([S:22][C:23]2[C:24]([CH3:25])=[N:14][N:13]([C:9]3[N:8]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[N:12]=[CH:11][N:10]=3)[C:27]=2[CH3:28])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 7226463-[(4-Chlorophenyl)sulfanyl]pentane-2,4-dioneHCID 22174882HCID 22174882, compound

Product 1

HCID 22174886HCID 22174886, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
95 °C

Procedure

A stirred suspension of the product of step 3 (0.333 g, 1.77 mmol) and 3-(4-chloro-phenylsulfanyl)-pentane-2,4-dione (0.473 g, 1.95 mmol) in n-propanol was heated at 95° C. overnight. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid. This material was further purified by trituration with diethyl ether to afford 0.056 g (8%) of product as a white solid: 1H NMR (DMSO-d6) δ 9.44 (s, 1H), 8.94-8.77 (m, 1H), 8.68-8.43 (m, 1H), 8.18-7.96 (m, 1H), 7.77-7.57 (m, 1H), 7.45-7.24 (m, 2H), 7.20-6.98 (m, 2H), 2.83 (s, 3H), 2.20 (s, 3H) ppm.

Workup

  1. concentrationThe reaction solution was concentrated directly onto silica and flash
  2. customchromatographed (methylene chloride/methanol)
  3. customto afford a dirty yellow solid
  4. customThis material was further purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-7580eca9d6e34fcfacf0d466b4a0ea4b
Source dataset
uspto-grants-2013_08
Patent number
US08518999B2

Reaction notes

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