Dimethylamine, hydrochloride → HCID 53728357, compound

HRID 1108302Notes

Reaction equation

HRID 1108302 reaction equation
Cl[N:2]1[C:6](=O)CC[C:3]1=O.[CH3:9][O:10][C:11]1[C:19]2[O:18][C:17]([S:20]([OH:22])=[O:21])=[CH:16][C:15]=2[CH:14]=[CH:13][CH:12]=1.[Li].Cl.CNC>ClCCl.O1CCCC1.C(N(CC)CC)C>[CH3:3][N:2]([CH3:6])[S:20]([C:17]1[O:18][C:19]2[C:11]([O:10][CH3:9])=[CH:12][CH:13]=[CH:14][C:15]=2[CH:16]=1)(=[O:22])=[O:21]

Participants

8

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 31398ChlorosuccinimideHCID 3028194LithiumHCID 18784852HCID 18784852, compound

Product 1

HCID 53728357HCID 53728357, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

N-Chlorosuccinimide (1 g) was added portionwise to 7-methoxybenzofuran-2-sulfinic acid, lithium salt (1.47 g) in dichloromethane (15 ml) at 0-5° C. under an inert atmosphere. The reaction was stirred at this temperature for 15 minutes and then warmed to ambient temperature and stirred for a further 15 minutes. The mixture was then flushed through a pad of celite, washing well with dichloromethane. The solvent was removed in vacuo to give a tan solid as the crude intermediate. This intermediate was added to a stirred solution of dimethylamine hydrochloride (0.67 g) and triethylamine (2.2 ml) in tetrahydrofuran (20 ml) at 0-5° C. under an inert atmosphere. The reaction was stirred at this temperature for 1 h and then warmed to room temperature and stirred for a further 48 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (2×40 ml) and water (50 ml). The combined organic phases were washed with 1M hydrochloric acid (2×20 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was washed with hexane (40 ml) to give the title compound as a tan solid (0.88 g).

Workup

  1. stirringstirred for a further 15 minutes
  2. customThe mixture was then flushed through a pad of celite
  3. washwashing well with dichloromethane
  4. customThe solvent was removed in vacuo
  5. customto give a tan solid as the crude intermediate
  6. stirringThe reaction was stirred at this temperature for 1 h
  7. temperaturewarmed to room temperature
  8. stirringstirred for a further 48 h
  9. customThe solvent was removed in vacuo
  10. customthe residue partitioned between ethyl acetate (2×40 ml) and water (50 ml)
  11. washThe combined organic phases were washed with 1M hydrochloric acid (2×20 ml)
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated in vacuo
  14. washThe residue was washed with hexane (40 ml)

Sources & evidence

ORD record
ord-aa094e4149ba405482b45097aa909c39
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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