1,2-Dichloroethane → HCID 12449425, compound

HRID 1285286Notes

Reaction equation

HRID 1285286 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@H:15]([OH:16])[C:14](=[O:17])[NH:13][C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:5][CH:4]=1.O.O.O.O.O.O.O.O.[Ba].ClCCCl.Cl.[CH3:36][N:37]([CH3:41])[CH2:38][CH2:39]Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:39][CH2:38][N:37]([CH3:41])[CH3:36])[C:12]3[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 10804253HCID 10804253, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 57365471HCID 57365471, compound

Product 1

HCID 12449425HCID 12449425, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

0.2 g of triethylbenzylammonium chloride, 3 g of trans-(+)-2-(4'-methoxyphenyl)-3-hydroxy-2,3-dihydro-1,5-benzothiazepine-4(5H)-one and 6.4 g of barium octahydrate were added under vigorous stirring to 60 ml of 1,2-dichloroethane and 7 ml of water. A solution of 3.2 g of 2-(dimethylamino)-ethyl chloride-hydrochloride in 5 ml of water was added dropwise to the above mixture during 5 minutes. Stirring was continued at room temperature for 1 hour and then for 1.5 hours at 70°. After cooling to room temperature the aqueous phase was separated and discarded and the 1,2-dichloroethane was removed under vacuum. The residue was dissolved in 50 ml of toluene and then extracted with 50 ml of 3% HCl. The acidic extract was treated with an excess of a sodium bicarbonate solution and then extracted with 50 ml of toluene. The toluene was removed under vacuum to yield 3.5 g of trans (+)-2-(4' methoxyphenyl)-3-hydroxy-5-(2'-dimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepine-4(5H)-one; m.p. 115°-117°.

Workup

  1. waitfor 1.5 hours at 70°
  2. customwas separated
  3. customthe 1,2-dichloroethane was removed under vacuum
  4. dissolutionThe residue was dissolved in 50 ml of toluene
  5. extractionextracted with 50 ml of 3% HCl
  6. extractionThe acidic extract
  7. additionwas treated with an excess of a sodium bicarbonate solution
  8. extractionextracted with 50 ml of toluene
  9. customThe toluene was removed under vacuum

Sources & evidence

ORD record
ord-11a589637f4e487daafae95f88747b01
Source dataset
uspto-grants-1986_01
Patent number
US04566995

Reaction notes

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