Sulfuryl chloride → HCID 23041821, compound

HRID 2166022Notes

Reaction equation

HRID 2166022 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8](/[C:10](=[CH:18]/[CH3:19])/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:9]=1)(=[O:3])[CH3:2].S(Cl)([Cl:23])(=O)=O>C(Cl)(Cl)(Cl)Cl.C(O)(=O)C>[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:23])=[C:8](/[C:10](=[CH:18]/[CH3:19])/[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24648Sulfuryl chlorideHCID 13922713HCID 13922713, compound

Product 1

HCID 23041821HCID 23041821, compoundYield 6.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

78 g (0.28 mol) of tert.-butyl Z-2-(2-acetamidothiazol-4-yl)but-2-enoate are suspended in a mixture of 2 l of carbon tetrachloride and 15 ml of glacial acetic acid at 0° C. 43 g (0.32 mol) of sulphuryl chloride, dissolved in 600 ml of carbon tetrachloride, are added dropwise in the course of five hours, while stirring. The solution is extracted once with saturated sodium bicarbonate solution and once with water, dried and concentrated to about 200 ml. The product which has precipitated is filtered off with suction and washed with ether (53.4 g). The mother liquor is evaporated completely and a second fraction of the product (6 g) is obtained by crystallization of the residue with ether/ligroin. Yield: 59.4 g=67.8% of theory.

Workup

  1. additionare added dropwise in the course of five hours
  2. extractionThe solution is extracted once with saturated sodium bicarbonate solution and once with water
  3. customdried
  4. concentrationconcentrated to about 200 ml
  5. customThe product which has precipitated
  6. filtrationis filtered off with suction
  7. washwashed with ether (53.4 g)
  8. customThe mother liquor is evaporated completely

Sources & evidence

ORD record
ord-930e4db8fe0c417d9a467f71eb6d1e03
Source dataset
uspto-grants-1990_07
Patent number
US04943568

Reaction notes

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