Hydrochloric Acid → HCID 19806312, compound

HRID 1681336Notes

Reaction equation

HRID 1681336 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CN(C)C=O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[N:7][C:6]=2[CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 767274-(2-Chloroethyl)morpholineHCID 178527796HCID 178527796, compound

Product 1

HCID 19806312HCID 19806312, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolved in 5 ml of N,N-dimethylformamide was 1.00 g (5.0 mmol) of 5-chloro-2-mercaptobenzothiazole, and 0.26 g (10.8 mmol) of hydrogenated sodium were added to the solution, which was stirred at room temperature. One hour later, 0.93 g (5.0 mmol) of a hydrochloride of 2-chloroethylmorpholine were added to the suspension, which was then stirred for 2 hours at 80° C. The solution was diluted with 100 ml of chloroform, followed by addition of 100 ml of a 5% saline solution and washing. After separation of the chloroform layer, the organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residues were purified by silica gel chromatography to obtain 1.05 g of white crystalline powders (67% yield).

Workup

  1. additionwere added to the solution, which
  2. stirringwas then stirred for 2 hours at 80° C
  3. additionfollowed by addition of 100 ml of a 5% saline solution
  4. washwashing
  5. customAfter separation of the chloroform layer
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residues were purified by silica gel chromatography

Sources & evidence

ORD record
ord-6e8900c6eed742699d49def1d23984db
Source dataset
uspto-grants-1992_12
Patent number
US05171746

Reaction notes

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