N,N,N',N'-Tetramethylethylenediamine → HCID 59323461, compound

HRID 2390035Notes

Reaction equation

HRID 2390035 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].CN([CH2:21][CH2:22]N(C)C)C.[Li][CH:27]([CH2:29][CH3:30])[CH3:28].CON(C)[C:34](=[O:41])[C:35]1C=CC=CC=1>C1COCC1.O>[C:1]([O:5][C:6]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=1[CH2:16][C:34](=[O:41])[CH2:35][C:22]1[CH:21]=[CH:30][CH:29]=[CH:27][CH:28]=1)=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 569575N-Methoxy-N-methylbenzamideHCID 59323156HCID 59323156, compoundHCID 178418400CID 53628100

Product 1

HCID 59323461HCID 59323461, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under an argon gas stream, 573 mg of tert-butyl(3-chloro-2-methylbenzyl)carbamate was dissolved in 10 mL of THF, and 739 μL of TMEDA and 4.88 mL of s-BuLi (1.01 M THF solution) were sequentially added dropwise at −78° C. It was elevated to −30° C., followed by stirring at the same temperature for 5 minutes. It was cooled to −78° C. again, and a solution of 440 mg of N-methoxy-N-methylbenzamide in 3 mL of THF was added dropwise thereto. After stirring at −78° C. for 30 minutes, it was warmed to −30° C., followed by stirring for 2 hours, and it was further warmed to room temperature, followed by stirring for 1 hour. After completion of the reaction, water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (hexane:ethyl acetate=5:1) to obtain 527 mg (yield 63%) of a title compound as a white solid.

Workup

  1. customwas elevated to −30° C.
  2. stirringAfter stirring at −78° C. for 30 minutes
  3. temperatureit was warmed to −30° C.
  4. stirringby stirring for 2 hours
  5. temperatureit was further warmed to room temperature
  6. stirringby stirring for 1 hour
  7. additionwas added
  8. extractionfollowed by extraction with chloroform
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customwas purified

Sources & evidence

ORD record
ord-e19d6e03099f486c836a6ded4949e63a
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

Loading…