Dimethylcarbamoyl Chloride → HCID 86674695, compound

HRID 571876Notes

Reaction equation

HRID 571876 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N+:4]=1[O-])[CH3:2].[CH3:14][N:15](C)C(Cl)=O.C(N(CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[C:14]([C:5]1[CH:6]=[C:7]([CH:8]=[C:3]([CH2:1][CH3:2])[N:4]=1)[C:9]([O:11][CH3:12])=[O:10])#[N:15]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 866746964-Pyridinecarboxylic acid, 2-ethyl-, methyl ester, 1-oxide

Product 1

HCID 86674695HCID 86674695, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Under N2, 2-ethyl-4-(methoxycarbonyl)pyridine 1-oxide (0.165 g, 911 μmol, Eq: 1.00) was dissolved in Acetonitrile (4 ml). Dimethylcarbamylchlorid (108 mg, 92.1 μl, 1.00 mmol, Eq: 1.1), triethylamine (175 mg, 239 μl, 1.73 mmol, Eq: 1.9) and Trimethylsilylcyanid (280 mg, 355 μl, 2.82 mmol, Eq: 3.10) were added and the RM was stirred at 90° C. overnight. The RM became an orange solution. Control with TLC: the reaction was finished. At RT, the RM was partitioned between water and EtOAc. The organic phase was dried over MgSO4; filtered; concentrated in vacuo: 350 mg; NMR: T205185. The crude material was purified by flash chromatography (silica gel, 20 g, 5% to 50% EtOAc in heptane). Light yellow oil.

Workup

  1. customAt RT, the RM was partitioned between water and EtOAc
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (silica gel, 20 g, 5% to 50% EtOAc in heptane)

Sources & evidence

ORD record
ord-c4ec67bd28cc4c87a363c3394ab96407
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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