Dimethylformamide → HCID 21558108, compound

HRID 1579082Notes

Reaction equation

HRID 1579082 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[CH3:8][N:9]([CH3:12])[CH:10]=[O:11].C(N(CC)CC)C>O>[CH3:8][N:9]([CH3:12])[C:10](=[O:11])[C:3]([C:2]([Cl:7])([Cl:6])[Cl:1])=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6420Trichloroacetyl chlorideHCID 8471Triethylamine

Product 1

HCID 21558108HCID 21558108, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 273g (1.5 mole) portion of trichloroacetyl chloride was added over one hour to a stirred, cooled (5°C) portion of 330g (4.5 moles) of dimethylformamide. Nitrogen was passed over the solution throughout the reaction. A 152g (1.5 mole) portion of triethylamine was then added dropwise while keeping the temperature below 15°C. The mixture was stirred overnight at ambient temperature and then cooled to 5°C before 300 ml of water was added gradually. The organic products were extracted into ethyl ether, and the ethereal solution was washed with water, 10% hydrochloric acid, and with brine, dried over magnesium sulfate and concentrated. The residue was distilled under vacuum through a short-path still yielding 160g of pure N,N-dimethyl-3,3,3-trichloropyruvamide: Bp 80°-82° (0.2mm); ir(λmax, film) 5.7 (s), 6.0 (s), 9.45 (s), 11.6 (m) microns; nmr (δ , CDCl3) 3.0 and 3.05 (two singlets, 6H) ppm.

Workup

  1. customNitrogen was passed over the solution throughout the reaction
  2. customthe temperature below 15°C
  3. additionwas added gradually
  4. extractionThe organic products were extracted into ethyl ether
  5. washthe ethereal solution was washed with water, 10% hydrochloric acid
  6. dry with materialwith brine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe residue was distilled under vacuum through a short-path

Sources & evidence

ORD record
ord-529c6966b57346ce899750cbe855f1d7
Source dataset
uspto-grants-1976_02
Patent number
US03940458

Reaction notes

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