Hydrochloric Acid → HCID 53875379, compound

HRID 1982730Notes

Reaction equation

HRID 1982730 reaction equation
[CH:1]([NH:3][C:4]1[S:5][C:6]([Cl:16])=[C:7]([C:9](=O)[C:10]([O:12]CC)=[O:11])[N:8]=1)=[O:2].[OH-].[K+].Cl.[CH2:20]([O:23][NH2:24])[CH:21]=[CH2:22].C(=O)(O)[O-].[Na+]>O1CCCC1.N1C=CC=CC=1>[CH:1]([NH:3][C:4]1[S:5][C:6]([Cl:16])=[C:7]([C:9](=[N:24][O:23][CH2:20][CH:21]=[CH2:22])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 420841O-AllylhydroxylamineHCID 516892Sodium BicarbonateHCID 14326717Ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylate

Product 1

HCID 53875379HCID 53875379, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (2-formamido-5-chlorothiazol-4-yl)glyoxylate (40.0 g) was added to 1N aqueous solution of potassium hydroxide (305 ml) at ambient temperature and stirred for 10 minutes. The reaction mixture was adjusted to pH 2.0 with 10% aqueous hydrochloric acid under ice cooling. A solution of allyloxyamine (14.4 g) in tetrahydrofuran (200 ml) was added to the stirred suspension of the above mixture in pyridine (54.1 g) at ambient temperature and stirred for 4 hours at the same temperature. The resultant mixture was adjusted to pH 7.5 with a saturated aqueous solution of sodium bicarbonate, and washed with ethyl acetate. The separated aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure. The residue was washed with diisopropyl ether and collected by filtration to give 2-(2-formamido-5-chlorothiazol-4-yl)-2-allyloxyiminoacetic acid (syn isomer, 24.74 g), mp. 166° to 167° C.

Workup

  1. stirringstirred for 4 hours at the same temperature
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. washThe residue was washed with diisopropyl ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-62c38d478aca46c2bb9a9a23835e1fcb
Source dataset
uspto-grants-1986_06
Patent number
US04596829

Reaction notes

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