Sodium Bicarbonate → 2-(2-Aminoethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid

HRID 2231422Notes

Reaction equation

HRID 2231422 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=O)[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].Cl.Cl.[NH2:16][O:17][CH2:18][CH2:19][NH2:20].C(=O)(O)[O-].[Na+]>C(O)C.O>[NH2:20][CH2:19][CH2:18][O:17][N:16]=[C:9]([C:7]1[N:8]=[C:4]([NH:3][CH:1]=[O:2])[S:5][CH:6]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

Product 1

HCID 543766712-(2-Aminoethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acidYield 91.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(2-formamidothiazol-4-yl)glyoxylic acid (5.5 g.) in ethanol (100 ml.) was added a solution of 2-(aminooxy)ethylamine.dihydrochloride (4.1 g.) in water (50 ml). The resulting mixture was adjusted to pH 4 with an aqueous solution of sodium bicarbonate and stirred for 3 hours at room temperature. The reaction mixture was evaporated to a volume of 100 ml. and cooled. The resulting precipitates were collected by filtration, washed successively with cold-water and ethanol to give the title compound (6.5 g.), mp 213° to 214° C. (dec.).

Workup

  1. customThe reaction mixture was evaporated to a volume of 100 ml
  2. temperatureand cooled
  3. customThe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed successively with cold-water and ethanol

Sources & evidence

ORD record
ord-d1c4656ab68347a3bede1d5c7dc9b7a4
Source dataset
uspto-grants-1988_11
Patent number
US04782158

Reaction notes

Loading…