Dimethylformamide → HCID 14708119, compound

HRID 722356Notes

Reaction equation

HRID 722356 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1.C([Li])(C)(C)C.CN(C)[CH:22]=[O:23]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[O:23])[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:11])([CH3:13])[CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11506746HCID 11506746, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 14708119HCID 14708119, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a chilled (−78° C.), stirred solution of the amide (Step 1) (5.0 g, 0.024 mole) in tetrahydrofuran (100 mL) was added t-butyl lithium (1.7M in pentane, 32.4 mL, 0.055 mole) dropwise. Dimethylformamide (2.3 mL, 0.03 mole) was added dropwise at −78° C. over 3 hours and the mixture allowed to warm room temperature. The reaction was quenched with ice water (200 mL) and extracted with ethyl acetate. The resulting organic phase was dried over MgSO4 and was concentrated in vacuo to a volume of 20 mL. A white solid precipitated which was collected by filtration yielding the formylated product (3.24 g, 56%): mp 168.7–170.8° C. 1H NMR (CDCl3/300 MHz) 10.60 (br s, 1H), 9.88 (s, 1H), 8.57 (s, 1H), 8.00 (s, 1H), 1.28 (s, 9H). Anal. Calc'd for C11H13N2O2Cl: C, 54.89; H, 5.44; N, 11.64 Found: C, 54.87; H, 5.42; N, 11.40.

Workup

  1. temperatureto warm room temperature
  2. customThe reaction was quenched with ice water (200 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe resulting organic phase was dried over MgSO4
  5. concentrationwas concentrated in vacuo to a volume of 20 mL
  6. customA white solid precipitated which
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-b43fda93475945a586ec4f8030aadb41
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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