Hydrochloric Acid → 2-(2-Cyclohexen-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetic acid

HRID 371238Notes

Reaction equation

HRID 371238 reaction equation
C1(ON2C(=O)C3=CC=CC=C3C2=O)CCCC=C1.O.NN.Cl.[CH:23]1([O:29][NH2:30])[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]1.C([NH:33][C:34]1[S:35][CH:36]=[C:37]([C:39](=O)[C:40]([OH:42])=[O:41])[N:38]=1)=O.[OH-].[Na+].NC1SC=C(C(=O)C(O)=O)N=1.Cl>C(O)C.O>[CH:23]1([O:29][N:30]=[C:39]([C:37]2[N:38]=[C:34]([NH2:33])[S:35][CH:36]=2)[C:40]([OH:42])=[O:41])[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 24654Hydrazine hydrate (1:1)HCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-HCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 135771062-[(Cyclohex-2-en-1-yl)oxy]-1H-isoindole-1,3(2H)-dioneHCID 20274566(2-Cyclohexen-1-yl)oxyamine hydrochloride3×

Product 1

HCID 542913242-(2-Cyclohexen-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
60 °C

Procedure

A mixture of N-(2-cyclohexen-1-yl)oxyphthalimide (17.6 g) and hydrazine hydrate (7.2 g) in ethanol (180 ml) was stirred for 1.5 hours at 60° C. After the addition of water (100 ml) and conc.hydrochloric acid (20 ml) to the reaction mixture, the resulting mixture was filtered and the filtrate was evaporated. The remaining mixture was filtered to give the filtrate containing (2-cyclohexen-1-yl)oxyamine hydrochloride (Filtrate A). To a suspension of 2-(2-formamidothiazol-4-yl)glyoxylic acid (10.0 g) in water (50 ml) was added a solution of sodium hydroxide (4.4 g) in water (50 ml). The resulting mixture was stirred for 2.5 hours at room temperature and the mixture containing 2-(2-aminothiazol-4-yl)glyoxylic acid was adjusted to pH 7.0 with 10% hydrochloric acid and then thereto was added the above obtained Filtrate A. The mixture was stirred for 2 hours at room temperature. The reaction mixture was adjusted to pH 7.5 with 4N aqueous solution of sodium hydroxide and then evaporated. The residue was washed with ethyl acetate and then adjusted to pH 2.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water, dried over phosphorus pentoxide to give 2-(2-cyclohexen-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetic acid (syn isomer)(2.0 g).

Workup

  1. filtrationhydrochloric acid (20 ml) to the reaction mixture, the resulting mixture was filtered
  2. customthe filtrate was evaporated
  3. filtrationThe remaining mixture was filtered
  4. customto give the filtrate
  5. stirringThe resulting mixture was stirred for 2.5 hours at room temperature
  6. stirringThe mixture was stirred for 2 hours at room temperature
  7. customevaporated
  8. washThe residue was washed with ethyl acetate
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water
  11. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-eb9fec63de584435a5eeff854e200577
Source dataset
uspto-grants-1985_07
Patent number
US04529802

Reaction notes

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