2-Chloro-N,N-dimethylethylamine → HCID 12331767, compound

HRID 1578634Notes

Reaction equation

HRID 1578634 reaction equation
O[C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]3[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][Cl:20].[CH3:22][O-:23].[Na+]>ClC1C=CC=CC=1>[ClH:20].[ClH:20].[CH3:16][N:17]([CH3:21])[CH2:18][CH2:22][O:23][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]3[CH:12]=[CH:11][C:10]([O:13][CH2:19][CH2:18][N:17]([CH3:21])[CH3:16])=[CH:9][C:8]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 1204339HCID 1204339, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 12331767HCID 12331767, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 200 ml of chlorobenzene is added 16.1 g (0.0745 mole) of 2,8 -dihydroxydibenzothiophene, 16.8 g (0.156 mole) of 2-dimethylaminoethyl chloride and 8.3 g (0.154 mole) of sodium methoxide. The mixture is stirred and heated to reflux for 16 hours. The cooled reaction mixture is filtered and the filtrate is washed with several portions of water, then dried over anhydrous magnesium sulfate. The chlorobenzene solution is evaporated in vacuo. The oily residue is dissolved in ether and treated with ethereal hydrogen chloride to give 2,8-bis(2-dimethylaminoethoxy)dibenzothiophene dihydrochloride which is crystallized from methanol-butanone, M.P. 248°-250°C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours
  3. customThe cooled reaction mixture
  4. filtrationis filtered
  5. washthe filtrate is washed with several portions of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe chlorobenzene solution is evaporated in vacuo
  8. dissolutionThe oily residue is dissolved in ether
  9. additiontreated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-0f20f03988b744789d44ed1a6d7b9f72
Source dataset
uspto-grants-1976_02
Patent number
US03937835

Reaction notes

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