N,N,N',N'-Tetramethylmethanediamine → HCID 20148900, compound

HRID 569269Notes

Reaction equation

HRID 569269 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][Cl:14])[CH:5]=[CH:4][C:3]=1[O:16][CH3:17].[CH3:18][N:19]([CH2:21]N(C)C)[CH3:20].C(OC(=O)C)(=O)C.[OH-].[Na+]>>[CH3:18][N:19]([CH2:21][CH:10]([CH2:11][CH2:12][CH2:13][Cl:14])[C:9]([C:6]1[CH:5]=[CH:4][C:3]([O:16][CH3:17])=[C:2]([Cl:1])[C:7]=1[Cl:8])=[O:15])[CH3:20]

Participants

5

Reactant 4

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 20148901HCID 20148901, compound

Product 1

HCID 20148900HCID 20148900, compound

Conditions

Temperature
50 °C

Procedure

2,3-Dichloro-4-(5-chloropentanoyl)anisole (29.5 g, 0.1 mole) and N,N,N',N'-tetramethyldiaminomethane (25.5 g, 0.249 mole) were stirred and heated at 50° C. and then acetic anhydride (36.8 g, 0.36 mole) was added dropwise with stirring at such a rate that the temperature rose to 100° C. After heating at 95° C. for an additional 2 hours, the mixture was kept at ambient temperature for 15 hours, poured into crushed ice (400 g), strongly basified with 10 normal sodium hydroxide and extracted with ether. The ether extract was dried over Na2SO4 and the solvent removed in vacuo to give 2-(dimethylaminomethyl)-5-chloro-1-(2,3-dichloro-4-methoxyphenyl)-1-pentanone as a viscous oil.

Workup

  1. customrose to 100° C
  2. temperatureAfter heating at 95° C. for an additional 2 hours
  3. additionpoured
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialwas dried over Na2SO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2e41602982b048a29f7b77aebb25b960
Source dataset
uspto-grants-1988_03
Patent number
US04731470

Reaction notes

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