Dimethylcarbamoyl Chloride → HCID 66846820, compound

HRID 254178Notes

Reaction equation

HRID 254178 reaction equation
[CH:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N+:7]=1[O-])([CH3:3])[CH3:2].[CH3:13][N:14](C)C(Cl)=O>ClCCl>[CH:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 66846703HCID 66846703, compound

Product 1

HCID 66846820HCID 66846820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A stirred solution of 2-(isopropoxymethyl)pyridine-N-oxide (17.8 g, 0.11 mol) in dichloromethane (200 mL) at room temperature was treated with trimethylsilyl cyamide (17.65 mL, 0.132 mol) and dimethylcarbamyl chloride (12.18 mL, 0.132 mol), heated to 40° C. for 18 h, quenched with 2-M aqueous Na2CO3 solution (400 mL) and stirred for 2 h. The mixture was extracted with dichloromethane (2×200 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as an orange oil; NMR δH (400 MHz, CDCl3) 1.17-1.18 (6H, d, J 6 Hz), 3.67-3.76 (1H, sept J 6 Hz), 4.58 (2H, s), 7.74-7.76 (1H, d, J 8 Hz), 7.92-7.94 (1H, d, J 7.5 Hz) and 8.04-8.08 (1H, t, J 7.5 Hz)

Workup

  1. customquenched with 2-M aqueous Na2CO3 solution (400 mL)
  2. extractionThe mixture was extracted with dichloromethane (2×200 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6b031af9782448b9deb26fd92cefb4d
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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