Ethanol → 2-Hydroxyimino(thien-2-yl)acetic acid

HRID 2398124Notes

Reaction equation

HRID 2398124 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=O)[C:15]([OH:17])=[O:16].C(O)C>O>[OH:3][N:2]=[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)[C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 776942-Thiopheneglyoxylic acidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate2×

Product 1

HCID 736296442-Hydroxyimino(thien-2-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A cooled solution of hydroxylamine hydrochloride (0.884 g) and sodium bicarbonate (1.08 g) in water (20 ml.) was added to a cooled (0° ) solution of thien-2-yl-glyoxylic acid (2.0 g) and sodium bicarbonate (1.08 g) in water (20 ml.). After two days at 20° the solution was extracted with ether, cooled and acidified with concentrated hydrochloric acid. The resulting white solid was filtered off (0.564 g) and the filtrate was then thoroughly extracted with ether. The combined extracts were washed with brine, dried and concentrated. The solid residue was triturated with benzene to give the exime (synisomer) (1.05 g; 51%), m.p. 132°, λmax. (ethanol) 284 nm (Ε9,500),νmax. (Nujol) 2590 and 1706 (SO2H) and 1655 cm-1 (C=N), τ (DMSO-d6), -2.5 to -0.5 (broad multiplet; N-OH and COOH), 2.36 (multiplet; thienyl C-5 H) and 2.82 (multiplet; thienyl C-3 H and C-4 H).

Workup

  1. extractionAfter two days at 20° the solution was extracted with ether
  2. temperaturecooled
  3. filtrationThe resulting white solid was filtered off (0.564 g)
  4. extractionthe filtrate was then thoroughly extracted with ether
  5. washThe combined extracts were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe solid residue was triturated with benzene
  9. customto give the exime (synisomer) (1.05 g; 51%), m.p. 132°, λmax

Sources & evidence

ORD record
ord-4d413e2fdcc04aad915be969d592b811
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

Loading…