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

HRID 1729969

반응식

HRID 1729969 반응식
[OH:1][NH:2]Cl.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]>O>[OH:1][N:2]=[C:14]([C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)[C:15]([OH:17])=[O:16]

참가 물질

5

반응물 3

HCID 776942-Thiopheneglyoxylic acidHCID 149953Hydroxylamine, N-chloro-HCID 516892Sodium Bicarbonate2회

생성물 1

HCID 736296442-Hydroxyimino(thien-2-yl)acetic acid수율 51%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A cooled solution of hydroxylamino 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 oxime (syn-isomer) (1.05 g; 51%), m.p. 1320,λmax. (ethanol) 284 mm (ε9,500), νmax. (Nujol) 2590 and 1706 (CO2H) and 1655 cm-1 (C=N), (DMSO-d6), -2.5 to -9.5 (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).

후처리

  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

출처 및 근거

ORD 기록
ord-21d1ee193ee941c89a2135d4a666f620
출처 데이터셋
uspto-grants-1976_11
특허 번호
US03991046

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