N,N,N',N'-Tetramethylmethanediamine → HCID 18987655, compound

HRID 2396570Notes

Reaction equation

HRID 2396570 reaction equation
[C:1](OC(=O)C)(=O)C.[F:8][C:9]([F:27])([F:26])[C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[O:18])=[N:14][CH:15]=1.CN(CN(C)C)C>>[F:27][C:9]([F:8])([F:26])[C:10]1[CH:11]=[CH:12][C:13]([C:16](=[CH2:1])[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[O:18])=[N:14][CH:15]=1

Participants

4

Reactant 3

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 18987699HCID 18987699, compound

Product 1

HCID 18987655HCID 18987655, compound

Procedure

Acetic anhydride (19 mL, 21 g, 200 mmol) was added slowly to a stirring slurry of 2-(5-trifluoromethyl-2-pyridinyl)-1-(4-chlorophenyl)ethanone (12.1 g, 40.0 mmol) in bisdimethylaminomethane (22 mL, 16 g, 160 mmol) at 0° C. causing immediate solution. TLC showed complete conversion after 5 min and the mixture was partitioned between ether and water by adding these solvents and separating the layers. The organic layer was extracted with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to obtain 13 g (99 percent of theory) of the title compound as a red oil.

Workup

  1. customafter 5 min
  2. customthe mixture was partitioned between ether and water
  3. additionby adding these solvents
  4. customseparating the layers
  5. extractionThe organic layer was extracted with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bd7c8c0e4011478d963414d248df50c9
Source dataset
uspto-grants-1996_02
Patent number
US05493024

Reaction notes

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