Sulphinylbis(dimethylamide) → HCID 19800527, compound

HRID 1647033Notes

Reaction equation

HRID 1647033 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]([OH:16])=O.[CH3:17][N:18]([CH3:24])S(=O)N(C)C>C(Cl)(Cl)Cl>[CH3:17][N:18]([CH3:24])[C:14](=[O:16])[CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:6][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 77385Sulphinylbis(dimethylamide)HCID 19800531HCID 19800531, compound

Product 1

HCID 19800527HCID 19800527, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 5-chloro-2-phenylthiazol-4-yl-acetic acid (1.98 g, 7.8 mmol), tetramethylsulphurous diamide (1.01 g, 9 mmol) and chloroform (dry, 30 ml) were heated under reflux for 4 hours. The reaction mixture was cooled and was concentrated under reduced pressure. The residue was taken up into chloroform (100 ml) and H2O (50 nl) and an excess of sodium bicarbonate added. After filtration the chloroform layer was washed with dilute HCl, water, dried (MgSO4), filtered and was concentrated under reduced pressure. The product was purified from hot petroleum ether (100°-126° C.) (0.47 g) m.p. 77°-79° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationwas concentrated under reduced pressure
  5. additionan excess of sodium bicarbonate added
  6. filtrationAfter filtration the chloroform layer
  7. washwas washed with dilute HCl, water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationwas concentrated under reduced pressure
  11. customThe product was purified from hot petroleum ether (100°-126° C.) (0.47 g) m.p. 77°-79° C.

Sources & evidence

ORD record
ord-6beb732fdcff45158aece746f6080b5b
Source dataset
uspto-grants-1993_01
Patent number
US05182402

Reaction notes

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