Sulfuryl chloride → HCID 13536862, compound

HRID 414792Notes

Reaction equation

HRID 414792 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([O:6]/[N:7]=[C:8](/[C:14](=[O:16])[CH3:15])\[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1=[O:17].S(Cl)([Cl:21])(=O)=O>C(Cl)Cl>[NH:1]1[CH2:5][CH2:4][C@H:3]([O:6]/[N:7]=[C:8](/[C:14](=[O:16])[CH2:15][Cl:21])\[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1=[O:17]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 13536858HCID 13536858, compound

Product 1

HCID 13536862HCID 13536862, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.4 g of ethyl (Z)-2-[((3S)-2-pyrrolidon-3-yl)-oxyimino]-3-oxo-n-butyrate are dissolved in 15 ml of methylene chloride, and 1.6 g of sulfuryl chloride are added thereto. The mixture is stirred at 15° to 25° C. for 20 hours. Then, the mixture is concentrated under reduced pressure to remove solvent. The residue is dissolved in chloroform, and the solution is washed with water. The chloroform solution is dried and concentrated under reduced pressure to dryness. Ethyl (Z)-2-[((3S)-2-pyrrolidon-3-yl)oxyimino]-3-oxo-4-chloro-n-butyrate is thereby obtained as crude product. The crude product thus obtained is dissolved in 20 ml of ethanol, and one g of thiourea and 1.2 g of N,N-dimethylaniline are added thereto. The mixture is stirred at 20° to 25° C. for 2 hours. Then, the mixture is concentrated under reduced pressure to remove solvent. The residue is dissolved in chloroform, and the solution is washed with water and an aqueous sodium bicarbonate solution, successively. The chloroform solution is dried and concentrated under reduced pressure to remove solvent. The residue is crystallized with isopropanol, and the crystals are collected by filtration. 1.2 g of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-[((3S)-2-pyrrolidon-3-yl)oxyimino]acetate are obtained.

Workup

  1. concentrationThen, the mixture is concentrated under reduced pressure
  2. customto remove solvent
  3. dissolutionThe residue is dissolved in chloroform
  4. washthe solution is washed with water
  5. dry with materialThe chloroform solution is dried
  6. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-9f2a7c5dd35843d7a587200c46b470ec
Source dataset
uspto-grants-1988_12
Patent number
US04794186

Reaction notes

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