Hydrochloric Acid → HCID 54142236, compound

HRID 328453Notes

Reaction equation

HRID 328453 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[C:7]([OH:9])=[O:8].C(=O)(O)[O-].[Na+].Cl.[C:17]([O:21][NH2:22])([CH3:20])([CH3:19])[CH3:18].Cl>O>[C:17]([O:21][N:22]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:7]([OH:9])=[O:8])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 776942-Thiopheneglyoxylic acidHCID 516892Sodium Bicarbonate2×HCID 2777906O-tert-butylhydroxylamine hydrochloride

Product 1

HCID 54142236HCID 54142236, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of thien-2-ylglyoxylic acid (6.2g.) and sodium bicarbonate (3.36g.) in water (100 ml.) was added dropwise to a stirred solution of t-butoxyamine hydrochloride (5.65 g.) and sodium bicarbonate (3.78g.) in water (100 ml.) at 0°-5° and the mixture was stirred at room temperature for 18 hr. The mixture was acidified with 2N hydrochloric acid to pH 2.0 and extracted with ethyl acetate. The combined extracts were washed with water, dried and concentrated to give a solid (9.75 g.). Recrystallisation from petroleum (b.p. 60°-80°) gave the title compound (4.0 g., 44%), m.p. 106°-107°, λmax. (EtOH) 290 nm (ε11,600), τ (CDCl3) values include 2.46, 2.66, 2.98 (d doublets, thienyl protons), 8.60 (C(CH3)3).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid (9.75 g.)
  6. customRecrystallisation from petroleum (b.p. 60°-80°)

Sources & evidence

ORD record
ord-573eceeec5b64f36ac6810ea91156c8e
Source dataset
uspto-grants-1977_04
Patent number
US04017515

Reaction notes

Loading…