Dimethylformamide dimethyl acetal → HCID 73316425, compound

HRID 1170457Notes

Reaction equation

HRID 1170457 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:16])[CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH3:15])=[O:11].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:16])[C:9](=[CH:19][N:20]([CH3:22])[CH3:21])[C:10]([NH:12][CH2:13][CH2:14][CH3:15])=[O:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 16736832HCID 16736832, compound

Product 1

HCID 73316425HCID 73316425, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 789 mg (3.29 mmol) of 2-chloro-β-oxo-N-propyl-benzenepropanamide in 5 mL of CH2Cl2 was treated with neat N,N-dimethylformamide dimethylacetal (450 μL, 402 mg, 3.38 mmol) added dropwise via syringe. The reaction was allowed to stir overnight and then concentrated in vacuo. Flash chromatography (11 cm in a 5 cm column) eluting with 2% MeOH/CH2Cl2 afforded 756 mg (79%) of the title compound as a yellow foam. Trituration with hexanes gave a yellow solid, mp 76-78° C.

Workup

  1. additionadded dropwise via syringe
  2. concentrationconcentrated in vacuo
  3. washFlash chromatography (11 cm in a 5 cm column) eluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-ea2fe09938b74f14a69d236075a23580
Source dataset
uspto-grants-2010_11
Patent number
US07825278B2

Reaction notes

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