2-Chloro-N,N-dimethylethylamine → HCID 70439652, compound

HRID 235682Notes

Reaction equation

HRID 235682 reaction equation
[H-].[Na+].[OH:3][C@H:4]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][C:9]2=[CH:20][CH:21]=[CH:22][C:23]3=[CH:24][CH:25]=[CH:26][C:7](=[C:8]23)[NH:6][C:5]1=[O:27].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31]Cl>CS(C)=O>[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][N:6]1[C:5](=[O:27])[C@@H:4]([OH:3])[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[S:10][C:9]2=[CH:20][CH:21]=[CH:22][C:23]3=[CH:24][CH:25]=[CH:26][C:7]1=[C:8]23

Participants

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 86741263HCID 86741263, compound

Product 1

HCID 70439652HCID 70439652, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 0.415 g of sodium hydride (58% dispersion in mineral oil) in 50 mL dimethyl sulfoxide (dried over CaH2) was stirred under nitrogen at 70° (bath temperature) for 1 hour then allowed to cool to room temperature. To this mixture 2.8 g of (±)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5-thiazocin-4(5H)-one was added then stirred at room temperature for 30 minutes. After the dropwise addition of 1.2 g of 2-dimethylaminoethyl chloride in 10 mL dimethyl sulfoxide, the mixture was heated at 50° for 30 minutes, then poured on 50 mL of ice-water. The aqueous solution was extracted with ethyl acetate (3×40 mL). The combined extracts were washed with brine (40 mL) and dried (magnesium sulfate). Removal of the solvent gave 3.1 g (92%) of crude (±)-trans-2,3-dihydro-5[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)naphtho[1,8-bc]-1,5 -thiazocin-4(5H)-one. For analysis a sample of this compound was crystallized from ethyl acetate, mp 157°-158°.

Workup

  1. stirringthen stirred at room temperature for 30 minutes
  2. temperaturethe mixture was heated at 50° for 30 minutes
  3. extractionThe aqueous solution was extracted with ethyl acetate (3×40 mL)
  4. washThe combined extracts were washed with brine (40 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-47ebbfed7fbc4853b4475f17298f4e77
Source dataset
uspto-grants-1987_02
Patent number
US04640930

Reaction notes

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